Water → 1-Benzyloxy-(4-methylsulfanylbenzyl)benzene

HRID 554506Notes

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]([S:30][CH3:31])=[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]([S:30][CH3:31])=[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 (1.23 mL, 7.72 mmol) and a boron trifluoride-diethyl ether complex (0.88 mL, 5.48 mmol) were added to a solution of (2-benzyloxy-phenyl)-(4-methylsulfanylphenyl)-methanol (2.13 g, 6.3 mmol) in acetonitrile (15 mL) at −40° C. and the mixture solution was stirred at the same temperature for 1.5 hours and further at 0° C. for 30 minutes, and then 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 (1.9 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 (1:10)]

Sources & evidence

ORD record: ord-496fbf8482264c2abfa287ed2a2af56d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048897B2

Reaction notes

Loading…