Water → HCID 178458874, compound

HRID 1084664Notes

Reaction equation

HRID 1084664 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[C:7]([C:11]1[C:12](=[O:31])[CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2C2C=CC(O)=CC=2)[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:8][CH3:9].FC1[CH:34]=[C:35]([CH2:39][S:40]([CH2:43]C2C=CC=C(F)C=2)(=[O:42])=[O:41])C=CC=1.O>CS(C)=O>[C:7]([C:11]1[C:12](=[O:31])[CH2:13][CH:14]([C:18]2[CH:19]=[CH:20][C:21]([O:4][C:2]3[CH:3]=[CH:34][CH:35]=[C:39]([S:40]([CH3:43])(=[O:42])=[O:41])[CH:1]=3)=[CH:22][CH:23]=2)[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 53523344HCID 53523344, compoundHCID 178458829HCID 178458829, compound

Product 1

HCID 178458874HCID 178458874, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1.7 g (15.0 mmol) of potassium t-butoxide in 20 mL of methyl sulfoxide at room temperature was treated with 2.0 g (7.7 mmol) of 2-propionyl-3-hydroxy-5-((4-hydroxyphenyl)-phenyl)cyclohex-2-en-1-one. After 15 minutes of stirring, 2.0 g (11 mmol) of 3-fluorophenylmethylsulfone was added thereto and the solution was heated, under nitrogen, at 120° C. for 7 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 light green oil. The product was recovered in a yield of 2.5 g (78 percent of theoretical). A small sample was crystallized to reveal the product as a white solid which melted at 109.5°-113.5° C. 1H NMR (CDCl3) δ1.17 (t, J=7 Hz, 3H, --CH2CH3), 2.63-3.65 (m includes s at 3.03 for CH3SO2 --, 10H), 6.97-7.78 (m, 8H, aromaties), 18.1 (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 light green oil
  8. customThe product was recovered in a yield of 2.5 g (78 percent of theoretical)
  9. customA small sample was crystallized

Sources & evidence

ORD record
ord-84ae7acf66c54c0e9e3a67527da8331d
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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