Water → 5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol

HRID 748813Notes

Reaction equation

HRID 748813 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH2:21][CH:22]([CH3:42])[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>[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])[CH:22]([CH3:42])[CH2:21][CH2:20][CH2:19][OH:18])(=[O:26])=[O:25])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 597509082-[5-(t-Butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene

Product 1

HCID 597508955-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanolYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 2-[5-(t-butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene (isomer mixture) (1.40 g, 2.23 mmol) obtained in Example 38 was dissolved in tetrahydrofuran (30 ml), followed by the addition of a tetrahydrofuran solution (1.0M, 5.0 ml, 5.0 mmol) of tetrabutylammonium fluoride under ice cooling. The resulting mixture was stirred at room temperature for 14 hours. After addition of water (3 ml), the residue obtained by concentrating the resulting mixture under reduced pressure was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol (isomer mixture) (879 mg, quant.) was obtained as a colorless oil.

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

Sources & evidence

ORD record
ord-cff27b7cf6044356aee32c7b00960042
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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