Imidazole → Methyl 6-tert-butyldimethylsiloxy-2,5,7,8-tetramethylchroman-2-acetate

HRID 1978355Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[C:11]([CH3:28])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:27])([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:14][CH2:13]2.N1C=CN=C1>CN(C=O)C.C(=O)([O-])O.[Na+].C(OCC)C>[O:9]([C:10]1[C:11]([CH3:28])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:27])([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:14][CH2:13]2)[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen, 5.41 g (35.9 mM) of tert-butyldimethylsilyl chloride was added to a solution of 7.69 g (27.63 mM) of methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetate and 2.82 g (41.4 mM) of imidazole in DMF (54 ml) at room temperature and the mixture was stirred at 0° C. for 20 hours. This reaction mixture was poured in saturated aqueous sodium hydrogen carbonate-diethyl ether under intense agitation to stop the reaction and, then, extracted with diethyl ether. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (ethyl acetate-hexane: 10%) to provide the title compound as yellow oil.

Workup

customthe reaction
extractionextracted with diethyl ether
washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
dry with materialdried over MgSO4
customThe resulting crude product was purified by column chromatography (ethyl acetate-hexane: 10%)

Sources & evidence

ORD record: ord-f5473daa4da244e6a54127b09db2b451
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235731B1

Reaction notes

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