Water → HCID 59750870, compound

HRID 748791Notes

Reaction equation

HRID 748791 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 59750857HCID 59750857, compound

Product 1

HCID 59750870HCID 59750870, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

The (E)-2-[5-(t-butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-3-pentenyl]-1,4-difluorobenzene (Isomer 246-B) (465 mg, 0.761 mmol) obtained in Example 246 was dissolved in tetrahydrofuran (10 ml), followed by the dropwise addition of a tetrahydrofuran solution (1.0M, 1.5 ml, 1.5 mmol) of tetrabutylammonium fluoride. At room temperature, the mixture was stirred for 1 hour. After addition of water (0.2 ml), the residue obtained by concentrating the resulting mixture under reduced pressure 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 (225 mg, 0.605 mmol, 80%) was obtained as a white powder.

Workup

  1. customthe residue obtained
  2. concentrationby concentrating the resulting mixture under reduced pressure
  3. customthe fraction obtained from the hexane
  4. concentrationethyl acetate=2:1 eluate was concentrated under reduced pressure
  5. customto give a white solid

Sources & evidence

ORD record
ord-2156d5067a24437bb948600148b804e9
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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