Chlorotrimethylsilane → Acetic acid, (phenylthio)-, methyl ester

HRID 1785769Notes

Reaction equation

HRID 1785769 reaction equation
[C:1]1([S:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si](C)(C)[CH3:14]>CO>[C:1]1([S:7][CH2:8][C:9]([O:11][CH3:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 59541(Phenylthio)acetic acid

Product 1

HCID 123375Acetic acid, (phenylthio)-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A room temperature solution of (phenylsulfanyl)acetic acid (8.4 g, 50.0 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (13 mL, 100.0 mmol), stirred for 16 hours, and concentrated. The concentrate was dissolved in 5:1/hexanes:diethyl ether, filtered through a pad of silica gel (80 g), rinsed with 5:1/hexanes:diethyl ether, and concentrated to provide the desired product.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in 5:1/hexanes
  3. filtrationdiethyl ether, filtered through a pad of silica gel (80 g)
  4. washrinsed with 5:1/hexanes
  5. concentrationdiethyl ether, and concentrated

Sources & evidence

ORD record
ord-578975c2636e4ffab55f5f133df6995d
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…