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

HRID 2085690Notes

Reaction equation

HRID 2085690 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-cf160fb464784415be7a239c41d23812
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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