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

HRID 2356024Notes

Reaction equation

HRID 2356024 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-528591ccfb9343e6b07fe0c4e10076fc
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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