Imidazole → 2-[(Tert-butyldimethylsilyl)oxymethyl]-6-methylbenzylalcohol

HRID 1766915Notes

Reaction equation

HRID 1766915 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[C:3]=1[CH2:10][OH:11].N1C=CN=C1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].O>O1CCCC1>[Si:21]([O:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[CH2:10][OH:11])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 22155097(3-Methyl-1,2-phenylene)dimethanol

Product 1

HCID 211104532-[(Tert-butyldimethylsilyl)oxymethyl]-6-methylbenzylalcoholYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methyl-1,2-benzenedimethanol (4.16 g, 27.3 mmol) obtained from Example 22-(1) in tetrahydrofuran (50 ml) was cooled to 0° C., and imidazole (1.86 g, 27.3 mmol) and tert-butylchlorodimethylsilane (4.12 g, 27.3 mmol) were added thereto. The mixture was stirred at room temperature for 3 hours, and then after adding water, the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, then the solvent was distilled off under reduced pressure, and the residue was subjected to chromatography on a silica gel (120 g) column (eluent; ethyl acetate:hexane=1:4) to afford the title compound (4.93 g, 68% yield) as a colorless oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5429a040818c44a0b8b7cf3ef0571ffe
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

Loading…