Water → [2-[2-[(4-Chlorophenyl)sulfonyl]-2-(2,5-difluorophenyl)ethyl]phenyl]methanol

HRID 748812Notes

Reaction equation

HRID 748812 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH:27]([C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=1[F:45])[S:28]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C(OC(C)C)(C)C>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([S:28]([CH:27]([C:38]2[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=2[F:45])[CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][OH:18])(=[O:30])=[O:29])=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59028246HCID 59028246, compound

Product 1

HCID 59750731[2-[2-[(4-Chlorophenyl)sulfonyl]-2-(2,5-difluorophenyl)ethyl]phenyl]methanolYield 85%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (20 ml) was dissolved 2-[2-[2-[(t-butyldiphenylsilyloxy)methyl]phenyl]-1-[(4-chlorophenyl)sulfonyl]ethyl]-1,4-difluorobenzene (1.10 g, 1.66 mmol), followed by the dropwise 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=1:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with diisopropyl ether, whereby the title compound (595 mg, 1.41 mmol, 85%) was obtained as a white powder.

Workup

  1. customthe residue obtained
  2. concentrationby concentrating the resulting mixture under reduced pressure
  3. customThe fraction obtained from the hexane
  4. concentrationethyl acetate=1:1 eluate was concentrated under reduced pressure
  5. customto give a white solid

Sources & evidence

ORD record
ord-5614270d1789412689c3c0599c8fc3f9
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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