Imidazole → 4-tert-Butyldimethylsilyloxybenzeneacetic Acid Methyl Ester

HRID 1878757Notes

Reaction equation

HRID 1878757 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.N1C=CN=C1.Cl[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[Si:19]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:12])=[CH:6][CH:7]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 137534164-tert-Butyldimethylsilyloxybenzeneacetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxyphenylacetic acid methyl ester (2000 mg, 12036 μmol), 1H-imidazole (2048 μl, 18053 μmol), and chloro-tert-butyldimethylsilane (1814 mg, 12036 μmol) in DMF (10 mL) was stirred at 23° C. for 18 h. The mixture was partitioned between EtOAc (50 mL) and 5% NaHCO3 (25 mL). The organic layer was dried over MgSO4 and concentrated to a colorless oil from toluene under reduced pressure. MS (ESI pos. ion) m/z (MH+): 281. Calc'd exact mass for C15H24O3Si: 280.

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and 5% NaHCO3 (25 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated to a colorless oil from toluene under reduced pressure

Sources & evidence

ORD record
ord-c7c454d95dec460d8e7017c8c08b3aa6
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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