1-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne → 4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

HRID 35884Notes

Reaction equation

HRID 35884 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C:15]1([S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]([OH:38])([CH3:37])[C:33]([F:36])([F:35])[F:34])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[F:36][C:33]([F:34])([F:35])[C:32]([OH:38])([CH3:37])/[CH:31]=[CH:30]/[C:27]1[CH:26]=[CH:25][C:24]([S:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:23])=[O:22])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 199393031-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 98635074,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-eneYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of sodium bis(2-methoxyethoxy)aluminum hydride (1.5 mL, 3.4M in toluene) in freshly distilled diethyl ether (6 mL) was added a solution of 1-(4-phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne in diethyl ether (6 mL) dropwise. The rate of addition was controlled so that the reaction temperature did not exceed 8° C. The mixture was stirred for 15 minutes and was quenched at 0° C. with 3N sulfuric acid (15 mL). Water (10 mL) was added and the product was extracted into diethyl ether. The combined organic extracts were washed (brine) and dried. The solvent was evaporated and the material was purified by chromatography, with chloroform:diethyl ether (25:1) as the eluent, to give the title compound (848 mg, 79%).

Workup

  1. additionThe rate of addition
  2. customdid not exceed 8° C
  3. customwas quenched at 0° C. with 3N sulfuric acid (15 mL)
  4. additionWater (10 mL) was added
  5. extractionthe product was extracted into diethyl ether
  6. washThe combined organic extracts were washed (brine)
  7. customdried
  8. customThe solvent was evaporated
  9. customthe material was purified by chromatography, with chloroform:diethyl ether (25:1) as the eluent

Sources & evidence

ORD record
ord-3e72d68742ee4716988a5c53520c7d6c
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Reaction notes

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