Gross, Hans published the artcileα-Halo ethers. XII. Preparation of N-substituted pyrroles from 2,5-dicblorotetrahydrofuran, Product Details of C10H9NO, the publication is Chemische Berichte (1962), 2270-5, database is CAplus.
cf. CA 56, 12838b. 2,5-Di-Cl (I), 2,5-di-PrO (II), 2,5-di-AcO (III), and 2,5-di-BzO (IV) derivatives of tetrahydrofuran with primary amino derivatives gave in good yields the corresponding N-substituted pyrroles. The appropriate amine (0.065-0.07 mole) in 5 cc. dry dioxane treated dropwise with shaking during 1 min. with 2.82 g. I, boiled briefly, diluted after 15 min. with 20 cc. H2O, and steam distilled, and the distillate extracted with Et2O yielded the corresponding pyrrole; method A. The appropriate primary amine (0.015-0.018 mole) in 5 cc. dry C5H5N treated dropwise with 1.41 g. I, diluted with 50 cc. H2O, acidified weakly with dilute HCl, and steam distilled or filtered gave the corresponding pyrrole derivative; method B. II (1.88 g.) and 0.013-0.015 mole amine and a granule of p-MeC6H4SO3H refluxed a few min. with the removal of the PrOH, cooled, diluted with dilute AcOH, and filtered or steam distilled gave the corresponding pyrrole; method C; the runs with o-C6H4(NH2)2, p-HOC6H4NH2, and p-O2NC6H4NH2 were refluxed 5-10 min. with 3 cc. AcOH instead of the p-MeC6H4SO3H. III (1.88 g.) and 0.013-0.015 mole amine in 5 cc. AcOH refluxed 5 min., cooled, diluted with 50 cc. H2O, and filtered gave the corresponding pyrrole; method D; the crude products from the runs with 2.21 g. IV were stirred with dilute NH4OH and filtered; in the run with IV and cyclohexylamine the product was isolated by steam distillation By these methods were prepared the following 1-substituted pyrroles (1-substituent, m.p. or b.p./mm., % yield, starting material, and method used are given): Bu, 62-3°/18 (n22D 1.4734), 53, I, A; C7H15, 104.5-7.5°/12 (n22D 1.4717), 50, I, A; cyclohexyl (V), 95°/10 (n21D 1.5125), 54, I, A; V, –, 50D, IV; PhCH2, 116-19°/11 (n19D 1.5690), 53, I, A; Ph, 61-2°, 64, I, B; Ph, –, 85, II, C; Ph, –, 65, IV, D; p-MeC6H4 (VI), 80-2°, 76, I, B; VI, –, 93, II, C; VI, –, 84, III, D; VI, –, 89, IV, D; 1-C10H7, 40°, 57, III, D; p-HOC6H4, 119-21°, 81, II, C; p-MeOC6H4 (VII), 111-13°, 65, I, B; VII, –, 57, II, C; VII, –, 68, III, D; VII, –, 68, IV, D; o-H2NC6H4, 97-9°, 57, II, C; p-O2NC6H4 (VIII), 180-1°, 87, II, C; VIII, –, 83, III, D; VIII, –, 96, IV, D; PhOCO, 46-7°, 28, II, C. H2NCH2CO2Et (IX) (3.2 g.) in 5 cc. dioxane treated dropwise with stirring and cooling with 1.41 g. I during 2 min., warmed after 20 min., kept 3 hrs. at room-temperature, diluted with 40 cc. H2O, and extracted with Et2O, and the residue from the extract shaken 2 hrs. with concentrated NH4OH and evaporated after 24 hrs. yielded 750 mg. 1-pyrrylacetamide, m. 166-7° (EtOAcEt2O-petr. ether). IX treated in the usual manner with I, shaken 2 hrs. with aqueous N2H4, and kept 24 hrs. at room temperature yielded 36% 1-pyrrylacethydrazide, m. 119-21° (EtOAc-Et2O-petr. ether). MeCH(NH2)CO2Et (1.7 g.) in 5 cc. C5H5N with 1.41 g. I and then with concentrated NH4OH yielded 30% α-(1-pyrryl)propionamide, m. 90-2° (EtOAc-Et2O-petr. ether). AcNH2 (3.8 g.) in 10 cc. warm Me2CO treated dropwise with 2.82 g. I, refluxed 20 min. with stirring, filtered, and evaporated, and the residue steam distd, gave 20% 1-acetylpyrrole, b12 70-1°, n21D 1.5107. BzNH2 (3 g.) in 20 cc. dioxane treated with about 2 g. Na2SO4, refluxed 10 min. with 2.82 g. I, cooled, diluted with 80 cc. H2O, and extracted with Et2O, and the residue steam distilled gave 1.0 g. colorless oil which boiled briefly with dilute aqueous NaOH and acidified gave 0.66 g. BzOH; the crude oily product consisted of at least 92% of 1-benzoylpyrrole. PhCH2CONH2 (1.4 g.) in 10 cc. MePh and 1.41 g. I refluxed 3 min., cooled, washed, and evaporated gave 0.77 g. 1-phenylacetylpyrrole, m. 72-4°. O-Butylurethan (2.4 g.) in 15 cc. MePh refluxed 3 min. with 2.82 g. I, the mixture worked up in the same manner, and the crude product steam distilled yielded 49% 1-carbobutoxypyrrole, b12 97°, n21 1.4670. PhNHNH2 and I (1.1 mole equivalent) gave by method B (CH2CH:NNHPh)2, yellowish leaflets, m. 123-4° (80% EtOH). PhCH2O2CNHNH2 and I gave similarly (CH2CH:NNHCO2CH2Ph)2, needles, m. 219-21° (HCONMe2).
Chemische Berichte published new progress about 23351-09-9. 23351-09-9 belongs to alcohols-buliding-blocks, auxiliary class Pyrrole,Benzene,Alcohol, name is 4-(1H-Pyrrol-1-yl)phenol, and the molecular formula is C10H9NO, Product Details of C10H9NO.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts