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. 3973-18-0, name is Propynol ethoxylate, molecular formula is C5H8O2, 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. Quality Control of Propynol ethoxylate
General procedure: 4-hydroxy-2-butanone (20, 1.00 g, 11.35 mmol) was pipetted into a dry flask and cooled to 0C under nitrogen atmosphere. 7N methanolic ammonia (11.2 mL, 79 mmol) was added via syringe, and the solution was allowed to stir at 0C for 3 hours. A solution of hydroxylamine-O-sulfonic acid (1.476 g, 13.05 mmol) in methanol (9.7 mL) was added dropwise, then was allowed to stir for an additional 16 hours while slowly warming to room temperature. The reaction was filtered through a sintered glass funnel, then transferred to a reaction vessel and re-cooled to 0C. Triethylamine (1.58 mL,11.35 mmol) was added, then molecular iodine (2.88 g, 11.35 mmol) was added slowly in 10 equal portions until the purple/brown color of iodine persisted in the reaction vessel. The solvent was removed under reduced pressure, and purification of the crude isolate via Kugelrohr distillation (60C, 1-3 torr) delivered the 2,2-diazirinyl intermediate as a clear oil (304 mg, 27% yield). A portion of this intermediate (300 mg, 3.00 mmol) was dissolved in dry pyridine (6 mL) and cooled to 0C in an ice bath. To this solution was added p-toluenesulfonyl chloride (628 mg, 3.30 mmol). The reaction mixture was allowed to stir for 24 hours at 0-4C, then was poured into a mixture of 37%w/v HCl (15 mL) and ice (80 mL). The resulting suspension was extracted 3x with ether, then the pooled organic layers were washed with 1N HCl solution, 1N NaOH solution, water, and brine. The organic extract was dried over MgSO4, vacuum filtered, and concentrated to a clear oil (428 mg, 15% yield over 3 steps) used without further purification. TLC Rf (2:1 hex:EtOAc) = 0.6. 1HNMR (500 MHz, CDCl3) delta 7.82 (d, J = 7.9 Hz, 2H), 7.37 (d, J= 7.9 Hz, 2H), 3.96 (t, J = 6.4 Hz, 2H), 2.46 (s, 3H), 1.68 (t, J= 6.4 Hz, 2H), 1.01 (s, 2H).
With the rapid development of chemical substances, we look forward to future research findings about 3973-18-0.
Reference:
Article; Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1538 – 1544;,
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