Imidazole → 2-(tert-Butyl-dimethyl-silanyloxy)-ethoxyl-ethanol

HRID 1255965Notes

Reaction equation

N1C=CN=C1.[CH2:6](O)[CH2:7][O:8][CH2:9][CH2:10][OH:11].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[OH2:21]>CN(C=O)C>[C:16]([Si:13]([CH3:15])([CH3:14])[O:11][CH2:10][CH2:9][O:8][CH:7]([OH:21])[CH3:6])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of imidazole (2.11 grams, 31 mmol) and diethylene glycol (5 grams, 47 mmol) in dry DMF (11 ml) was cooled to 0° C. and stirred for 30 minutes under argon atmosphere. A solution of tert-butyldimethylsilyl chloride (4.72 grams, 31 mmol) in dry DMF (15 ml) was added dropwise and the resulting mixture was maintained for 2 hours at 0° C. and was then allowed to warm up to room temperature. Water (180 ml) was thereafter added and the resulting solution was extracted with ethyl acetate (4×80 ml). The combined organic extracts were washed with brine, the solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography, using ethyl acetate as eluent, to give the product (Compound 28a) as a white oil (4.65 grams, 45% yield).

Workup

temperatureto warm up to room temperature
extractionthe resulting solution was extracted with ethyl acetate (4×80 ml)
washThe combined organic extracts were washed with brine
customthe solvent was removed under reduced pressure
customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-db806b9fb28a447fadcd31a2875df3cc
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461166B2

Reaction notes

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