Methyl trifluoromethyl ketone → 1,1,1-Trifluoro-2-methyl-3-(4-phenylsulfonylphenoxy)propan-2-ol

HRID 35880

Reaction equation

HRID 35880 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:15])([F:14])[C:11](=[O:13])[CH3:12].[C:16]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O.O1CCCC1.O>[F:9][C:10]([F:15])([F:14])[C:11]([CH3:2])([OH:13])[CH2:12][O:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:23])=[O:24])=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 9871Methyl trifluoromethyl ketoneHCID 24758Sodium hydride2×HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 3438044-(Benzenesulfonyl)phenol

Product 1

HCID 199393161,1,1-Trifluoro-2-methyl-3-(4-phenylsulfonylphenoxy)propan-2-olYield 9.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A suspension of trimethylsulfoxonium iodide (1.6 6 g, 7.56 mmol) and sodium hydride (0.36 g, 7.56 mmol of 50% in oil) was stirred in 25 mL of dimethylsulfoxide for 25 minutes. The mixture was cooled to 10° C. and was treated with a solution of trifluoroacetone (0.72 g, 6.41 mmol) in tetrahydrofuran (3 mL). After stirring for 20 minutes, the solution was allowed to warm to room temperature where it was treated with a solution of 4-(phenylsulfonyl)phenol (1.5 g, 6.40 mmol) and sodium hydride (0.31 g, 6.4 .mmol of 50% in oil) in dimethylsulfoxide (7.5 mL). The mixture was stirred for 1 hour and then heated to 50° C. for 18 hours. The reaction was poured into water, acidified to pH 6, and extracted with diethylether. The combined organic fractions were evaporated to give an oil. Chromatography, eluting with dichloromethane yielded the title compound as a tan solid (0.22 g); mp 94°-96° C.; NMR: 1.39 (s,3, CH3), 4.12 (q,2, CH2), 6.39 (s,1, OH), 7.17 (s,1, Ar), 7.20 (s,1, Ar), 7.63 (m,3, Ar), 7.91 (m,4, Ar); MS: m/z=361(M+1). Analysis for C16H15F3O4S: Calculated: C, 53.33; H, 4.20; Found: C, 53.54: H, 4.25.

Workup

  1. temperatureto warm to room temperature where it
  2. stirringThe mixture was stirred for 1 hour
  3. temperatureheated to 50° C. for 18 hours
  4. extractionextracted with diethylether
  5. customThe combined organic fractions were evaporated
  6. customto give an oil
  7. washChromatography, eluting with dichloromethane

Sources & evidence

ORD record
ord-ec5b7bac7a3c49c0a56de6b59478deb2
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Linked notes

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