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

HRID 748694Notes

Reaction equation

HRID 748694 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.N1C=CC=CC=1.F.C(=O)(O)[O-].[Na+].CCCCCC>C(Cl)Cl>[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

6

Reactant 4

HCID 8058HexaneHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 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 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[5-(t-butyldiphenylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene (Isomer 38-A) (710 mg, 1.13 mmol) obtained in Example 38 was dissolved in methylene chloride (20 ml). Under ice cooling, hydrogen fluoride-pyridine (0.64 ml) was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. To the reaction mixture was added a saturated aqueous solution (20 ml) of sodium bicarbonate, followed by extraction with diethyl ether. The organic layer was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to yield a colorless oil. The resulting colorless oil was solidified with hexane, whereby the title compound (283 mg, 64%) was obtained as a white powder.

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed successively with 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)
  9. customto yield a colorless oil

Sources & evidence

ORD record
ord-796c89a19477411d9203348a2f467949
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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