Triethylamine → ((e)-4,4,4-Trifluoro-but-2-ene-2-sulfonyl)-benzene

HRID 1352386Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[CH2:3][C:4](I)([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:5].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[F:17][C:2]([F:1])([F:16])/[CH:3]=[C:4](/[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:7])=[O:8])\[CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 14.0 mmol rac-(4,4,4-trifluoro-2-iodo-butane-2-sulfonyl)-benzene in 25 ml tetrahydrofuran and 2.5 ml water were added 42.1 mmol triethylamine and 42.1 mmol potassium carbonate. The mixture was heated at 70° C. for 6 h. The reaction mixture was then diluted with ethyl acetate and was washed sequentially with 1 N hydrochloric acid and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a yellow oil (yield 72%). EI-MS (m/e): 250.1 (M+, 15%), 186.1 ([M−SO2]+, 38%), 125.0 (PhSO+, 100%), 77.1 (Ph+, 38%).

Workup

washwas washed sequentially with 1 N hydrochloric acid and brine
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-cdf1384b9e194c5ba61795dafa168031
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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