Imidazole → 4-(t-Butyldimethylsiloxy)methyl-1-t-butyldiphenylsiloxy-3,5-dimethoxybenzene

HRID 49286Notes

Reaction equation

[O:1]([C:19]1[CH:26]=[C:25]([O:27][CH3:28])[C:22]([CH2:23][OH:24])=[C:21]([O:29][CH3:30])[CH:20]=1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CN=C1.[C:36]([Si:40](Cl)([CH3:42])[CH3:41])([CH3:39])([CH3:38])[CH3:37].O>CN(C)C=O>[O:24]([CH2:23][C:22]1[C:21]([O:29][CH3:30])=[CH:20][C:19]([O:1][Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:26][C:25]=1[O:27][CH3:28])[Si:40]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:42])[CH3:41]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the crude 4-t-butyldiphenylsiloxy-2,6-dimethoxybenzyl alcohol (4.01 g) obtained by the above-described procedure in anhydrous dimethylformamide (30 mL) were added imidazole (1.29 g, 18.98 mmol) and t-butylchlorodimethylsilane (1.79 g, 11.86 mmol). After stirring at 50° C. for 4 hours, water was added and the resulting mixture was extracted with ethyl acetate-hexane (1:2). The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield crude 4-(t-butyldimethylsiloxy)methyl-1-t-butyldiphenylsiloxy-3,5-dimethoxybenzene was obtained as a colorless amorphous powder (5.33 g).

Workup

extractionthe resulting mixture was extracted with ethyl acetate-hexane (1:2)
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0e676e4988224e608baf0f35a6547731
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706703B2

Reaction notes

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