Imidazole → Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate

HRID 1171771Notes

Reaction equation

HRID 1171771 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CN=C1.[OH:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].O>CN(C=O)C>[Si:5]([O:14][CH:15]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C:16]([O:18][CH3:19])=[O:17])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 523496Methyl 2-hydroxy-2-(4-methoxyphenyl)acetate

Product 1

HCID 86623126Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBDMSCl (1.5 g, 9.94 mmol) and imidazole (1.0 g, 14.6 mmol) were added to a solution of methyl hydroxy-(4-methoxyphenyl)acetate (Teodozyj Kolasa et al., J. Org. Chem., 1987, 22, 4978-4984) (1.3 g, 6.62 mmol) in DMF (8 mL) and the mixture was stirred at r.t. for 2 h. Water was added and the mixture was extracted with diethyl ether. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to give the title compound (2.0 g, 97%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c065bb14b334bd5901077221dadb90f
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

Loading…