Chlorotrimethylsilane → Methyl (2-trimethylsilyloxyphenyl)acetate

HRID 1034292Notes

Reaction equation

HRID 1034292 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].Cl[Si:14]([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl.N1C=CC=CC=1>[CH3:15][Si:14]([CH3:17])([CH3:16])[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 24754724Methyl (2-trimethylsilyloxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2-hydroxyphenyl)acetate (1.5 g) in CH2Cl2 (10 mL) and pyridine (10 mL) was added slowly chlorotrimethylsilane (1.26 mL). The mixture was stirred for 18 hours, then most of the solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel using 15% of EtOAc in hexane to afford 1.3 g of methyl (2-trimethylsilyloxyphenyl)acetate.

Workup

  1. custommost of the solvent was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel using 15% of EtOAc in hexane

Sources & evidence

ORD record
ord-52105d15fb804481b83aff49f9328c58
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

Loading…