Реакция #50703

Уравнение реакции

NaOH

ethyl 3-(acetyl-thio)-2-methylpropanoate

→

title compound

Выход 82.2%

Ethyl 3-mercapto-2-methylpropanoate

Выход 82.2%

Растворители

MeOH

Условия реакции

Обработка

1. 1
   Экстракцияthe title thiol was extracted with EtOAc
2. 2
   Сушкаdried over MgSO4
3. 3
   Концентрированиеconcentrated
4. 4
   workup.DISTILLATIONdistilled

Методика

At -20° C., 3N NaOH (150 mL, 450 mmol) was added dropwise to a solution of ethyl 3-(acetyl-thio)-2-methylpropanoate (66.47 g, 349 mmol, Step 1) in 700 mL of MeOH and the mixture was stirred at that temperature for 30 min. 25% Aq NH4OAc was then added and the title thiol was extracted with EtOAc, dried over MgSO4, concentrated and distilled to yield 42.52 g (82%) of the title compound as an oil; bp: 96-98° C./15 mmHg. 1H NMR (CDC13): δ1.21-1.36 (6H, m), 1.50 (1H, t, SH), 2.66 (2H, m), 2.81 (1H, m), 4.19 (2H, q).

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