Diethyl Ether → Ethyl 2-(acetylthiomethyl)butanoate

HRID 1590095Notes

Reaction equation

HRID 1590095 reaction equation
[CH2:1]([C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[S:10]1C=CC=C1CC(O)=O.[CH3:19][CH2:20][O:21]CC>>[C:20]([S:10][CH2:9][CH:3]([CH2:1][CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:21])[CH3:19]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 159702-Thiopheneacetic acidHCID 291416Ethyl 2-methylidenebutanoate

Product 1

HCID 15025921Ethyl 2-(acetylthiomethyl)butanoate

Conditions

Temperature
65 °C

Procedure

Ethyl 2-ethyl-2-propenoate (Arch. Pharm., 313, 846 (1980)) (5 g, 39 mmol) was diluted with 5.6 mL (78 mmol) of thiolacetic acid and stirred at 65° C. for 36 hours. The mixture was then diluted with Et2O, washed with H2O and the organic phase was dried with Na2SO4. Evaporation to dryness yielded the title material as an orange oil which was used as such for the next step.

Workup

  1. washwashed with H2O
  2. dry with materialthe organic phase was dried with Na2SO4
  3. customEvaporation to dryness

Sources & evidence

ORD record
ord-66d3478a2fc44839b4dfc840e9eaa65c
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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