Water → HCID 22621288, compound

HRID 841183Notes

Reaction equation

HRID 841183 reaction equation
C([Li])(CC)C.[C:6]1([S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[C:17]([F:23])[CH:16]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:24][C:25]([F:30])([F:29])[C:26]([CH3:28])=[O:27].O>C1COCC1>[OH:27][C:26]([CH3:28])([C:25]([F:30])([F:29])[F:24])[C:22]#[C:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:14])=[O:13])=[CH:16][C:17]=1[F:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9871Methyl trifluoromethyl ketoneHCID 22621283HCID 22621283, compoundHCID 178418400CID 53628100

Product 1

HCID 22621288HCID 22621288, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

s-Butyllithium (0.24 ml of a 1.3M solution in hexanes) was added dropwise to a solution of 4-phenylsulphonyl-2-fluorophenylethyne (Method 28) (0.08 g) in dry THF (3 ml) at −50° C. After 25 minutes a solution of 1,1,1-trifluoroacetone (0.035 g) in dry THF (0.5 ml) was added and the mixture was allowed to warm to ambient temperature overnight. Water (10 ml) was added and THF was evaporated off under reduced pressure. The residue was diluted with water (30 ml) and extracted with ethyl acetate (30 ml). The organic layer was washed with brine then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-30% ethyl acetate/hexane then triturated with hexane to give the title compound (0.038 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 2.75 (s, 1H), 7.5-7.75 (m, 6H), 7.93 (d, 2H); EA: C17H12F4O3S requires C, 54.8; H, 3.3%; found: C, 54.4; H, 3.4%.

Workup

  1. customTHF was evaporated off under reduced pressure
  2. additionThe residue was diluted with water (30 ml)
  3. extractionextracted with ethyl acetate (30 ml)
  4. washThe organic layer was washed with brine
  5. customthen dried
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  8. washeluting with 0-30% ethyl acetate/hexane
  9. customthen triturated with hexane

Sources & evidence

ORD record
ord-fdec3c644f8848bca23248de1b52a101
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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