Sodium Hydroxide → (S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

HRID 35890Notes

Reaction equation

HRID 35890 reaction equation
[O:1]1[CH:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[C:2]1([CH3:24])[C:3]([F:6])([F:5])[F:4].[OH-].[Na+].C([O-])(O)=O.[Na+]>C(O)C>[F:6][C:3]([F:4])([F:5])[C@:2]([OH:1])([CH3:24])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[CH:11][C:12]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 19939309HCID 19939309, compound

Product 1

HCID 67708369(S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-eneYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-Epoxy-1,1,1-trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)butane (1.68 g) was dissolved in 250 mL ethanol and 150 mL 6N NaOH was added. The mixture was stirred for 2 hours, and 500 mL of saturated aqueous. NaHCO3 was added. The mixture was extracted with ether and the organic layers were combined, dried, and evaporated to yield the title compound as a white solid (1.2 g, 70%); [α]23 =-28.35 (c=1.05, MeOH); NMR (CDCl3): 7.93-7.85 (m,4, Ar), 7.58-7.45 (m,5, Ar), 6.90-6.84 (d,1, vinylic), 6.40-6.34 (d,1, vinylic), 2.75 (s,1, OH), 1.55 (s,3, CH3); MS: m/z=357(M+1).

Workup

  1. extractionThe mixture was extracted with ether
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-e3d7239607224effba93b0d1d37125ab
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Reaction notes

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