Pyridine, hydrofluoride (1:1) → 4-(4-Chlorophenylsulfonyl)-4-(2,5-difluorophenyl)-3-methyl-1-butanol

HRID 748784Notes

Reaction equation

HRID 748784 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]([CH3:31])[CH:12]([C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30])[S:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])(C(C)(C)C)(C)C.N1C=CC=CC=1.F.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH:12]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[CH:11]([CH3:31])[CH2:10][CH2:9][OH:8])(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 21226206Ethyl acetate hexaneHCID 59750761HCID 59750761, compound2×

Product 1

HCID 230288584-(4-Chlorophenylsulfonyl)-4-(2,5-difluorophenyl)-3-methyl-1-butanolYield 46.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 2-[4-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-2-methylbutyl]-1,4-difluorobenzene (Compound A (Isomer B)) (102 mg, 0.209 mmol) obtained in Example 237 was dissolved in tetrahydrofuran (3 ml), followed by the addition of hydrogen fluoride-pyridine (0.5 ml). The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, and then dried over magnesium sulfate. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (36.1 mg, 0.0963 mmol, 46%) was obtained as colorless columnar crystals.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solid thus obtained

Sources & evidence

ORD record
ord-e9a9530072474cc7992b8921f50ff3ad
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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