Water → 4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

HRID 35883Notes

Reaction equation

HRID 35883 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:22][C:19]([F:20])([F:21])[C:18]([OH:24])([CH3:23])/[CH:17]=[CH:16]/[C:13]1[CH:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 199393031-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yneHCID 21226445Aluminium lithium hydride

Product 1

HCID 98635074,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-eneYield 37.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne (0.45 g, 1.27 mmol) in tetrahydrofuran (6 mL) was added lithium aluminum hydride (56 mg, 1.4 mmol) in one portion and the reaction mixture stirred for 18 hours. The reaction mixture was then treated sequentially with water (0.4 mL), 2N sodium hydroxide (0.4 mL), and water (1 mL). After 10 minutes of stirring the reaction was filtered through diatomaceous earth and the precipitate washed with ethyl acetate. The aqueous layer of the filtrate was separated and extracted further with ethyl acetate. The combined organic extracts were dried filtered, and evaporated. The crude oil was purified by chromatography, with chloroform:ethyl acetate as eluent (18:1), to yield the title compound as a white solid (0.17 g, 37%); mp 94°-97° C.; 250 MHz NMR (CDCl3): 1.56 (s,3, CH3), 2.30 (s,1, OH), 6.38 (d,1, J=16.0, vinylic), 6.89 (d,1, J=16.0, vinylic), 7.46-7.60 (m,5, Ar), 7.89-7.96 (m,4, Ar); MS (EI): m/z=356 (M+). Analysis for C17H15F3O3S: Calculated: C, 57.29; H, 4.24; Found: C, 57.24; H, 4.32.

Workup

  1. stirringAfter 10 minutes of stirring the reaction
  2. filtrationwas filtered through diatomaceous earth
  3. washthe precipitate washed with ethyl acetate
  4. customThe aqueous layer of the filtrate was separated
  5. extractionextracted further with ethyl acetate
  6. customThe combined organic extracts were dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude oil was purified by chromatography, with chloroform

Sources & evidence

ORD record
ord-5b3f9132ba654f07bb0086b54313dd34
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Reaction notes

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