Butyl vinyl ether → HCID 59218935, compound

HRID 2247440Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)=[CH:5][C:4]=1OS(C(F)(F)F)(=O)=O.[CH:28]([O:30]CCCC)=[CH2:29].C1(C(C2C=CC=CC=2)(P)CC)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:28]([C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

357 mg of Methyl (4′-methoxy-3′-trifluoromethanesulfonyloxybiphenyl-3-yl)acetate was dissolved in 3 ml of N,N-dimethylformamide, then 0.45 ml of butyl vinyl ether, 10 mg of palladium acetate, 20 mg of diphenyl phosphinopropane and 1 ml of triethylamine were added thereto, and the mixture was stirred at 80° C. overnight in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 184 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

washwashed with 1N hydrochloric acid
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-99d5a50b596d4e309306b54ce27237a0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687664B2

Reaction notes

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