Pyridine, hydrofluoride (1:1) → HCID 59750780, compound

HRID 748781Notes

Reaction equation

HRID 748781 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:33])[CH:14]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])(C(C)(C)C)(C)C.N1C=CC=CC=1.F.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([CH:14]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[CH:13]([OH:33])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 21226206Ethyl acetate hexaneHCID 597508896-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-(2,5-difluorophenyl)-2-hexanol

Product 1

HCID 59750780HCID 59750780, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 6-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-(2,5-difluorophenyl)-2-hexanol (Isomer 234-A) (42.0 mg, 0.0809 mmol) obtained in Example 234 was dissolved in tetrahydrofuran (2 ml), followed by the addition of hydrogen fluoride-pyridine (0.2 ml). The resulting mixture was stirred at room temperature for 6 hours. The solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (16.7 mg, 0.0412 mmol, 51%) was obtained as a white powder.

Workup

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

Sources & evidence

ORD record
ord-30448c9b72124e5a8d7f09a34d3ab9e7
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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