Water → HCID 67458942, compound

HRID 554495

Reaction equation

C([SiH](CC)CC)C.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C(#N)C>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen stream, triethylsilane (2.8 mL, 17.6 mmol) and a boron trifluoride-diethyl ether complex (1.84 mL, 14.6 mmol) were added to a solution of (2-benzyloxyphenyl)-(4-chlorophenyl)methanol (4.76 g, 14.6 mmol) in acetonitrile (150 mL) at −40° C. and the reaction mixture was stirred at the same temperature for 2 hours and furthermore at 0° C. for one hour. Water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (3.85 g, 85%).

Workup

extractionthe mixture was extracted with methylene chloride
washThe organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialdried (anhydrous magnesium sulfate)
distillationthe solvent was distilled under reduced pressure
customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

Sources & evidence

ORD record: ord-57cc811cd4e742f1804956f546b65e37
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048897B2

Linked notes

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