Ethyl Thioglycolate → (4-Formyl-phenylsulfanyl)-acetic acid ethyl ester

HRID 1503641Notes

Reaction equation

HRID 1503641 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][SH:6])[CH3:2].[H-].[Na+].Br[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>CN(C=O)C>[CH:15]([C:14]1[CH:17]=[CH:18][C:11]([S:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:7])=[CH:12][CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 707414-Bromobenzaldehyde

Product 1

HCID 54431766(4-Formyl-phenylsulfanyl)-acetic acid ethyl esterYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was prepared according to general procedure E. To a solution of ethyl-2-mercaptoacetate (1.7 mmol) in dry DMF (5 ml), sodium hydride (2.0 mmol) was added at 0° C. After 10 minutes, 4-bromobenzaldehyde (1.4 mmol) was added and the mixture was heated for 3 hours. After cooling, the solvent was removed under reduced pressure. The residue was chromatogaphed on a silica gel column (cyclohexane/ethyl acetate 9/1 as eluent) to give 188 mg of ethyl 2-(4-formylphenythio)acetate (yield 59%). 1H NMR (250 MHz, CDCl3): δ 1.23 (t, J=7.5 Hz, 3H), 3.73 (s, 2H), 4.18 (q, 2H), 7.42 (d, J=8.75 Hz, 2H), 7.76 (d, J=8.75 Hz, 2H), 9.93 (s, 1H).

Workup

  1. customThe compound was prepared
  2. temperaturethe mixture was heated for 3 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-22987d5b8d604cb38f784decc27e75f9
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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