Water → HCID 59750936, compound

HRID 748790Notes

Reaction equation

HRID 748790 reaction equation
[Si]([O:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH:23]([C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[F:41])[S:24]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.CCCCCC>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([S:24]([CH:23]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[F:41])[CH2:22]/[CH:21]=[CH:20]\[CH2:19][OH:18])(=[O:26])=[O:25])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59750790HCID 59750790, compound

Product 1

HCID 59750936HCID 59750936, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

In tetrahydrofuran (5 ml) was dissolved (Z)-2-[5-(t-butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-3-pentenyl]-1,4-difluorobenzene (Isomer 246-A) (145 mg, 0.237 mmol). After dropwise addition of a tetrahydrofuran solution (1.0M, 0.5 ml, 0.5 mmol) of tetrabutylammonium fluoride, the mixture was stirred at room temperature for 2 hours. Water (0.2 ml) was added to the reaction mixture, followed by concentration under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with hexane, whereby the title compound (51 mg, 0.137 mmol, 58%) was obtained as a white powder.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customThe residue thus obtained
  3. concentrationethyl acetate=2:1 eluate was concentrated under reduced pressure
  4. customto give a white solid

Sources & evidence

ORD record
ord-a55b4577d8f34e40a603cd86286019bc
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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