HCID 56949563, compound → Ethyl 3-mercapto-2-methylbutanoate

HRID 2093246Notes

Reaction equation

HRID 2093246 reaction equation
C([S:4][CH:5]([CH3:13])[CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)C>Cl.C(O)C>[SH:4][CH:5]([CH3:13])[CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 56949563HCID 56949563, compound

Product 1

HCID 20656016Ethyl 3-mercapto-2-methylbutanoateYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

The crude product of Example 1 prior to column chromatography (˜9 g) was refluxed with 10 mL ethanol and several drops of 10M HCl (in ethanol) for 12 hours. Distillation (8.5 T, 75° C.) afforded the free thiol as a clear oil (3.7 g, 52%) and as a mixture of stereoisomers. Odor: at 1 ppm in DPG—guava, mango, exotic fruity note, juicy, sweet, tropical and ripe. GC/MS (EI): m/z (%) 162(34), 134(2), 129(34), 89(52), 74(77), 56(100). 1H NMR (CDCl3); δ 4.08-4.17 (m, 2H), 3.14-3.31 (m, 1H), 2.46-2.58 (m, 1H), 1.67 & 1.50 (2d, J=7.79 Hz, 1H mix of diastereomers), 1.17-1.35 (m, 9H)). 13C NMR (CDCl3) for mix of diastereomers: δ 174.6, 60.9, 60.6, 48.8, 47.7, 37.8, 23.6, 21.9, 14.3, 13.5.

Workup

  1. distillationDistillation (8.5 T, 75° C.)

Sources & evidence

ORD record
ord-b57a0879db8748958b02715a6681c8f4
Source dataset
uspto-grants-2013_05
Patent number
US08445051B2

Reaction notes

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