Imidazole → 2-[(tert-Butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcohol

HRID 1766908Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[C:4]=1[CH2:11][OH:12].N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O>O1CCCC1>[Si:22]([O:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:11][OH:12])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Methoxy-1,2-benzenedimethanol (1.30 g, 7.73 mmol) obtained from Example 21-(1) was dissolved in tetrahydrofuran (15 ml), and imidazole (526.2 mg, 7.73 mmol) and tert-butylchlorodimethylsilane (1.165 g, 7.73 mmol) were added thereto at 0° C. with stirring. The mixture was stirred at room temperature for 2 hours, then water was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel (60 g) column (eluent; ethyl acetate:hexane=1:4) to afford the title compound (1.156 g, 53% yield) as an oil.

Workup

stirringThe mixture was stirred at room temperature for 2 hours
extractionthe product was extracted with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-253902a73572476d84f71ec61421d186
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230023B2

Reaction notes

Loading…