Ethyl Thioglycolate → HCID 60631860, compound

HRID 1503640Notes

Reaction equation

HRID 1503640 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][SH:6])[CH3:2].[H-].[Na+].F[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]>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])=[C:12]([N+:19]([O-:21])=[O:20])[CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 5981294-Fluoro-3-nitrobenzaldehyde

Product 1

HCID 60631860HCID 60631860, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl-2-mercaptoacetate (0.7 mmol) in dry DMF (2.5 ml), sodium hydride (0.85 mmol) was added 0° C. After 15 minutes, 4-fluoro-3-nitrobenzaldehyde (0.7 mmol) was added and the mixture was heated at 60° C. overnight and monitored by TLC until completion. After cooling, the solvent was removed under reduced pressure. The residue was chromatogaphed on a silica gel column (cyclogexane/ethyl acetate 4/1 as eluent) to give 46 mg of ethyl 2-(4-formyl-2-nitrophenylthio)acetate as yellow compound (yield 24%). 1H NMR, (250 MHz, CDCl3): δ 1.25 (t, J=7.5 Hz, 3H), 3.80 (s, 2H), 4.21 (q, J=7.75, 2H), 7.64 (d, J=9.75, 1H), 8.03 (d, J=9.75, 1H), 8.68 (s, 1H), 10.00 (s, 1H) 13C NMR (126 MHz, CDCl3): δ 15.4, 36.5, 63.8, 128.5, 129.3, 133.9, 145.6, 147.1, 169.5, 190.1.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-915bdae046d14a7abd8ee1720df454c7
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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