Methyl Thioglycolate → 118286-24-1

HRID 1898942Notes

Reaction equation

HRID 1898942 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[H-].[Na+].[CH:9](Br)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[C:10]1([CH:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[S:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 236603Bromodiphenylmethane

Product 1

HCID 11231102118286-24-1Yield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl thioglycolate (5.95 g, 56 mmol) in 225 mL of tetrahydrofuran is added sodium hydride (2.5 g of 60% NaH in oil, 62.5 mmol). The mixture is stirred at room temperature for 10 minutes. Benzhydryl bromide (Aldrich of Milwaukee, Wis.; hereinafter "Aldrich") (15.3 g, 62 mmol) is added and the reaction mixture is stirred at room temperature for 3 days and then concentrated in vacuo. The residue is taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate, 10% aqueous citric acid, and brine and then dried over magnesium sulfate. Chromatography on silica gel, eluting with 4% ethyl acetate in hexane provides methyl [[(diphenyl)methyl]thio]acetate as a colorless oil in 15% yield.

Workup

  1. additionhereinafter "Aldrich") (15.3 g, 62 mmol) is added
  2. stirringthe reaction mixture is stirred at room temperature for 3 days
  3. concentrationconcentrated in vacuo
  4. washwashed with saturated aqueous sodium bicarbonate, 10% aqueous citric acid, and brine
  5. dry with materialdried over magnesium sulfate
  6. washChromatography on silica gel, eluting with 4% ethyl acetate in hexane

Sources & evidence

ORD record
ord-29e91dd8b92946d38904017ecd4e16bf
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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