Acetic Acid → Ethyl 2-(mercaptomethyl)butanoate
Reaction equation
C([S:4][CH2:5][CH:6]([CH2:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)C.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[SH:4][CH2:5][CH:6]([CH2:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the thioester of Step 1 (5.00 g, 24.5 mmol) in MeOH (15 mL) at 0° C., under nitrogen, was added K2CO3 (9.67 g, 73.5 mmol). The resulting mixture was stirred at 0° C. for a half hour, and then AcOH (8.82 g, 147 mmol) and 25% aq NH4OAc were added. The title compound was extracted with EtOAc, dried over Na2SO4 and purified by distillation on a Kugelrohr apparatus (200° C., 760 mm Hg). Yield: 1.700 g, 45%. 1H NMR (CD3COCD3): δ 0.86 (3H, t), 1.25 (3H, t), 1.65 (2H, quintet), 1.78 (1H, t), 2.45 (1H, quintet), 2.68 (2H, m), 4.15 (2H, q).
Workup
- extractionThe title compound was extracted with EtOAc
- dry with materialdried over Na2SO4
- distillationpurified by distillation on a Kugelrohr apparatus (200° C., 760 mm Hg)
Sources & evidence
- ORD record
- ord-4338deb0c4864c80b4cf488acbc2aad0
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05266568
Reaction notes
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