Methyl trifluoromethyl ketone → HCID 22419841, compound
Reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][CH:16]=[N:15][C:14]=3[CH:18]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[F:27][C:28]([F:33])([F:32])[C:29](=[O:31])[CH3:30]>O1CCCC1>[F:27][C:28]([F:33])([F:32])[C:29]([C:16]1[S:17][C:13]2[CH:12]=[CH:11][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])=[CH:18][C:14]=2[N:15]=1)([OH:31])[CH3:30]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of 5-phenylsulfonylbenzothiazole (0.845 g) in dry tetrahydrofuran (50 mL) at -78° C. was added lithium diisopropylamide (3.5 mmol in 3 mL tetrahydrofuran) dropwise over approximately 10 minutes. A deep red solution formed. Trifluoroacetone (0.63 g) was added. After stirring for 20 minutes at -78° C., the reaction mixture was quenched with saturated ammonium chloride solution. The reaction mixture was then extracted with ether (75 mL and 25 mL) and dichloromethane (25 mL). The combined organic layers were dried, filtered and purified by chromatography, eluting with ethyl acetate:hexane (gradient of 10 to 30% ethyl acetate), to give the title compound as a white solid (0.558 g); m.p. 126.5°-128.5° C.; NMR: 8.62 (d,1), 8.43 (d,1), 8.01-8.07 (m,4), 7.60-7.70 (m,3), 1.84 (s,3); MS: m/z=388(M+1). Analysis for C16H 12 F3NO3S2 : Calculated: C,49.61; H,3.12; N, 3.62: Found: C, 49.43; H, 3.23; N, 3.56.
Workup
- customA deep red solution formed
- customthe reaction mixture was quenched with saturated ammonium chloride solution
- extractionThe reaction mixture was then extracted with ether (75 mL and 25 mL) and dichloromethane (25 mL)
- customThe combined organic layers were dried
- filtrationfiltered
- custompurified by chromatography
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-20bec1eff193464aaaa17d7cc81a580c
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05504089
Reaction notes
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