As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 39590-81-3
Example 136A {1-[(benzyloxy)methyl]cyclopropyl}methanol To a cold (0 C.) solution of 1,1-bis(hydroxymethyl)cyclopropane (5.00 g, 49.0 mmol) in N,N-dimethylformamide (100 ml) was added 60% sodium hydride in mineral oil (1.958 g, 49.0 mmol) in portionwise manner Benzylbromide (5.82 mL, 49.0 mmol) was added to the reaction mixture at room temperature resulting in a slight exotherm. The reaction mixture was stirred at room temperature for 18 hours, and partitioned between 1N HCl solution and methyl tert-butyl ether. The layers were separated and the aqueous layer was washed with CHCl3:isopropyl alcohol (120 mL:40 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by flash chromatography using a 220 gm cartridge, eluting with 10-70% methyl tert-butyl ether/heptanes to afford 6.58 g of the title product as colorless oil. (70% Yield)1H NMR (400 MHz, CDCl3) delta 0.45-0.51 (m, 2H), 0.51-0.57 (m, 2H), 2.46 (d, J=4.6 Hz, 1H), 3.46 (s, 2H), 3.56 (d, J=3.3 Hz, 2H), 4.54 (s, 2H), 7.27-7.39 (m, 5H). MS (ESI+): M+H=192.8.
The chemical industry reduces the impact on the environment during synthesis 39590-81-3, I believe this compound will play a more active role in future production and life.
Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
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