Ethyl Thioglycolate → HCID 54250288, compound

HRID 1074096Notes

Reaction equation

HRID 1074096 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Br[CH2:17][C:18]1C=CC2C(=CC=CC=2)[CH:19]=1.[H-].[Na+].SCC(OCC)=O>O1CCCC1>[CH:14]1[C:15]2[C:2](=[CH:1][CH:17]=[CH:18][CH:19]=2)[CH:3]=[CH:4][C:5]=1[CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 4107274Ethyl (4-methylbenzylthio)acetate

Product 1

HCID 54250288HCID 54250288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 29 for the preparation of ethyl (4-methylbenzylthio)acetate, starting with 2-bromomethylnaphthalene (20 g), sodium hydride (5.1 g) in a 50% strength dispersion in liquid paraffin and ethyl 2-mercaptoacetate (10.9 g) in tetrahydrofuran (200 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent, ethyl (2-naphthylmethylthio)acetate (12 g) is obtained, and is used in the crude state in the subsequent syntheses.

Workup

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent

Sources & evidence

ORD record
ord-37514ed6893941bdad726b6c7070bad3
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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