Water → HCID 59750822, compound

HRID 748687Notes

Reaction equation

HRID 748687 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32])[S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([CH:14]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59750708HCID 59750708, compound

Product 1

HCID 59750822HCID 59750822, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (30 ml) was dissolved 2-[6-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-1,4-difluorobenzene (0.70 g, 1.4 mmol). Under ice cooling, a tetrahydrofuran solution (1.0M, 4.2 ml, 4.2 mmol) of tetrabutylammonium fluoride was added and the mixture was stirred at room temperature for 1 hour. After addition of water (1.0 ml) to the reaction mixture, the mixture was concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=3:2) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (0.47 g, 86%) was obtained as a white powder.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:2)
  4. customto yield a white solid
  5. washThe resulting white solid was washed with hexane, whereby the title compound (0.47 g, 86%)
  6. customwas obtained as a white powder

Sources & evidence

ORD record
ord-9a51a6c294b04014b133b45c5e234c92
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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