Water → HCID 178458875, compound

HRID 1084663Notes

Reaction equation

HRID 1084663 reaction equation
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[C:7]([C:11]1[C:12](=[O:31])[CH2:13][CH:14]([C:18]2[CH:23]=CC=C[C:19]=2C2C=CC(O)=CC=2)[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:8][CH3:9].F[C:33]1[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1.O>CS(C)=O>[C:7]([C:11]1[C:12](=[O:31])[CH2:13][CH:14]([C:18]2[CH:19]=[CH:5][C:2]([O:4][C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=3)=[CH:3][CH:23]=2)[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 23665647Potassium tert-butoxideHCID 178458829HCID 178458829, compound

Product 1

HCID 178458875HCID 178458875, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1.7 g (15.0 mmol) of potassium t-butoxide in 15 mL of methyl sulfoxide at room temperature was treated with 2.0 g (11 mmol) of 2-propionyl-3-hydroxy-5-((4-hydroxyphenyl)-phenyl)cyclohex-2-en-1-one. After 20 minutes of stirring, 2.0 g (11 mmol) of (4-fluorophenyl)methyl sulfone was added thereto and the solution was heated, under nitrogen, at 100° C. for 2.5 hours. The mixture was cooled to room temperature, poured into 100 mL of cold water and washed with 30 mL of diether ether and acidified with 1N HCl to pH 4 and extracted thrice with 20 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and passed through a short column of silica gel. Evaporation of the solvent afforded the above named product as a solid residue which was recrystallized from absolute alcohol. The product was recovered in a yield of 2.4 g (75 percent of theoretical) and melted at 157-158° C. 1H NMR (CDCl3) δ1.18 (t, J=7 Hz, 3H, --CH2CH3), 2.70-3.58 (m includes s at 3.03 for CH3SO 2 --, 10H), 7.00-7.38 (m, 6H, aromatics), 7.89 (d, J=9 Hz, 2H, aromatics), 18.17 (s, 1H, enol H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with 30 mL of diether ether
  3. extractionextracted thrice with 20 mL portions of methylene chloride
  4. dry with materialThe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of the solvent
  7. customafforded the above named product as a solid residue which
  8. customwas recrystallized from absolute alcohol
  9. customThe product was recovered in a yield of 2.4 g (75 percent of theoretical) and melted at 157-158° C

Sources & evidence

ORD record
ord-828084cdb1734dd583343258a142a50a
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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