Hydrochloric Acid → HCID 178422383, compound

HRID 433221Notes

Reaction equation

HRID 433221 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[C:9](=[CH:22][C:23](=[S:34](=[O:36])=[O:35])[CH:24]([CH3:33])[C:25]=1[C:26]1[CH2:30][CH:29]([CH2:31]Cl)[O:28][N:27]=1)[C:10]([C:12]1[C:17](=[O:18])[CH:16]([CH3:19])[CH2:15][CH:14]([CH3:20])[C:13]=1[OH:21])=[O:11].Cl>CS(C)=O>[CH3:7][C:8]1[C:9](=[CH:22][C:23](=[S:34](=[O:36])=[O:35])[CH:24]([CH3:33])[C:25]=1[C:26]1[CH:30]2[CH:29]([CH2:31]2)[O:28][N:27]=1)[C:10]([C:12]1[C:17](=[O:18])[CH:16]([CH3:19])[CH2:15][CH:14]([CH3:20])[C:13]=1[OH:21])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 178422385HCID 178422385, compound

Product 1

HCID 178422383HCID 178422383, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

At room temperature, 0.27 g (2.4 mmol) of potassium tert-butoxide is added to a solution of 0.36 g (0.8 mmol) of 2-[2-methyl-3-(5-chloromethyl-4,5-dihydroisoxazol-3-yl)-4-methyl sulfonylbenzoyl]-1-hydroxy-4,6-dimethylcyclohex-1-en-3-one in 4 ml of dimethyl sulfoxide, and the mixture was stirred for 12 hours. The reaction mixture was then introduced into 300 ml of 3% strength hydrochloric acid. Following extraction with ethyl acetate, the combined organic phases were washed with water and dried, and the solvent was removed. This gave 0.21 g (63% of theory) of the title compound of melting point 90-96° C. 1H-NMR (δ in ppm): δ=1.0-1.6 (m, 10H), 2.18 (s, 3H), 2.4-2.5 (m, 2H), 2.77 (m, 1H), 3.20 (s, 3H), 5.18 (s, 1H), 7.31 (d, 1H), 8.02 (d, 1H).

Workup

  1. extractionextraction with ethyl acetate
  2. washthe combined organic phases were washed with water
  3. customdried
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-da23bcc90a8944859d84ba67005ac277
Source dataset
uspto-grants-2003_12
Patent number
US06667333B2

Reaction notes

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