Imidazole → 4-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol

HRID 1095107

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([Si:21]([CH3:24])([CH3:23])[O:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(2-hydroxy-ethoxy)-phenol (4.2 g, 27 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added imidazole (2.1 g, 31 mmol) and tert-butyldimethylchlorosilane (4 g, 27 mmol). The reaction mixture was then stirred at 0° C. for 1 h. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1;4) to give 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol as a colorless oil (5.1 g, 70%)

Workup

customThe mixture was partitioned between ethyl acetate and water
customOrganic layer was separated
extractionaqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography (EtOAc:hexanes=1;4)

Sources & evidence

ORD record: ord-ce0f28087fc84ddba86a8b087ffac0a1
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08134001B2

Linked notes

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