Water → (3'-(Hydroxymethyl)-6-methyl-4-[3-(methylsulfonyl)propoxy]biphenyl-2-yl)methyl acetate

HRID 416165

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=1)(=[O:3])[CH3:2].CC1C=CC(S(O[CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:9]=[C:8]([CH3:13])[C:7]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of [4-hydroxy-3′-(hydroxymethyl)-6-methylbiphenyl-2-yl]methyl acetate (1.02 g, 3.56 mmol) and 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (1.25 g, 4.27 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (0.640 g, 4.32 mmol), and the mixture was stirred at 90° C. for 21 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0) to give the title compound (0.87 g, yield 60%) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0)

Sources & evidence

ORD record: ord-4ea94a262f8e4381a177f4d348b98bb4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088821B2

Linked notes

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