Water → HCID 67459549, compound

HRID 554501Notes

Reaction equation

C([SiH]([CH2:6][CH3:7])CC)C.C(O[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]([CH:30]2[CH2:32][CH2:31]2)=[CH:26][CH:25]=1)O)C1C=CC=CC=1.[OH2:33]>C(#N)C>[CH2:22]([O:33][C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:24]2[CH:25]=[CH:26][C:27]([CH:30]3[CH2:31][CH2:32]3)=[CH:28][CH:29]=2)[CH:6]=[CH:29][CH:24]=[CH:25][CH2:26]1)[C:17]1[CH:16]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen stream, triethylsilane (0.73 mL, 4.6 mmol) and a boron trifluoride-diethyl ether complex (0.5 mL, 4.0 mmol) were added to a solution of (2-benzyloxyphenyl)-(4-cyclopropylphenyl)methanol (1.3 g, 4.0 mmol) in acetonitrile (7 mL) at −40° C. and the mixture solution was stirred at the same temperature for 1.5 hours and furthermore at 0° C. for 30 minutes. 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 (1:7)] to obtain the title compound (1.2 g, 95%).

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 (1:7)]

Sources & evidence

ORD record: ord-2a41c35473064ce6ab83143d03dc812e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048897B2

Reaction notes

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