Water → HCID 59750809, compound

HRID 748809Notes

Reaction equation

HRID 748809 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[F:43])[S:26]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)(=[O:28])=[O:27])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.CCCCCC>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([CH:25]([C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][OH:18])(=[O:28])=[O:27])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59750880HCID 59750880, compound

Product 1

HCID 59750809HCID 59750809, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

In tetrahydrofuran (20 ml) was dissolved 2-[7-(t-butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]heptyl]-1,4-difluorobenzene (786 mg, 1.23 mmol), followed by the dropwise addition of a tetrahydrofuran solution (1.0M, 4.0 ml, 4.0 mmol) of tetrabutylammonium fluoride under ice cooling. The resulting mixture was stirred at room temperature for 14 hours. After addition of water (2 ml), the mixture was concentrated 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 (403 mg, 1.00 mmol, 81%) was obtained as a white powder.

Workup

  1. concentrationthe mixture was concentrated 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-556c6fad47d64e00b6b7c0849ddf1283
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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