HCID 19939313, compound → HCID 19939317, compound

HRID 35889Notes

Reaction equation

HRID 35889 reaction equation
[F:1][CH:2]([F:25])[C:3]([CH:22]([F:24])[F:23])([OH:21])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[F:25][CH:2]([F:1])[C:3]([CH:22]([F:23])[F:24])([OH:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 19939313HCID 19939313, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19939317HCID 19939317, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4,4-difluoro-3-difluoromethyl-3-hydroxy-1-(4-phenylsulfonylphenyl)but-1-yne (555 mg, 1.49 mmol) in tetrahydrofuran (15 mL) was added LAH (65 mg, 1.71 mmol) in one portion and the mixture was allowed to stir for 18 hours. The reaction was quenched with Na2SO4.10H2O, filtered and evaporated. The resulting material was purified by chromatography, with diethyl ether:hexanes (60:40) as the eluent, followed by chromatography, with diethyl ether:hexanes (50:50) as the eluent. The resulting material was recrystalized from methyl tert-butylether:hexanes to give the title compound; mp 123.0°-123.5° C.; NMR (CDCl3): 7.93-7.88 (m,4, Ar), 7.59-7.47 (m,5, Ar), 7.03 (d,1, J=16.2, vinylic), 6.33 (d,1, J=16.2, vinylic), 5.89 (t,2, J=54.8, CF2H), 3.02 (s,1, OH); MS: m/z=375(M+1). Analysis for C17H14F4O3S: Calculated: C, 54.54; H, 3.77; Found: C, 54.30; H, 3.84.

Workup

  1. customThe reaction was quenched with Na2SO4.10H2O
  2. filtrationfiltered
  3. customevaporated
  4. customThe resulting material was purified by chromatography, with diethyl ether:hexanes (60:40) as the eluent
  5. customThe resulting material was recrystalized from methyl tert-butylether

Sources & evidence

ORD record
ord-f5d084b56dd74325969a16424319050b
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Reaction notes

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