Water → Methyl 4-(2-benzyloxybenzyl)benzoate

HRID 554532Notes

Reaction equation

C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)O)=[CH:13][CH:12]=1.O>C(#N)C>[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a nitrogen stream, triethylsilane (2.27 mL, 13.5 mmol) and a boron trifluoride-diethyl ether complex (1.52 mL, 11.88 mmol) were added to a solution of 4-[(2-benzyloxyphenyl)-hydroxymethyl]benzoic acid methyl ester (4.15 g, 11.9 mmol) in acetonitrile (22.7 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. 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 (2.39 g, 62%).

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-f83c07b9920244398148734d25103fa4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048897B2

Reaction notes

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