1,3-Cyclohexanedione → 3-Oxocyclohex-1-enyl 2-chloro-4-ethylsulfonyl-3-(3a,4,5,6a-tetrahydro-furo[3,2-d]isoxazol-3-yl)-benzoate

HRID 48145Notes

Reaction equation

HRID 48145 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[CH:15]3[CH2:16][CH2:17][O:18][CH:14]3[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:24]1(=O)[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1>ClCCl>[Cl:1][C:2]1[C:10]([C:11]2[CH:15]3[CH2:16][CH2:17][O:18][CH:14]3[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)=[O:5]

Participants

4

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 227421392-Chloro-4-ethylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]-isoxazol-3yl)benzoic acid

Product 1

HCID 227421303-Oxocyclohex-1-enyl 2-chloro-4-ethylsulfonyl-3-(3a,4,5,6a-tetrahydro-furo[3,2-d]isoxazol-3-yl)-benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.9 g (2.5 mmol) of 2-chloro-4-ethylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]-isoxazol-3yl)benzoic acid together with 0.31 g (2.8 mmol) of 1,3-cyclohexandione in 50 ml of dichloromethane are treated with 0.53 g (2.8 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimi hydrochloride and 0.1 g of N,N-dimethylaminopyridine. After the mixture has been stirred for 16 hours at room temperature, it is washed with 1 N hydrochloric acid and sodium chloride solution and dried over magnesium sulfate. It is filtered with suction and the filtrate is concentrated. This gives 0.66 g (58% of theory) of crude 3-oxocyclohex-1-enyl 2-chloro-4-ethylsulfonyl-3-(3a ,4,5,6a-tetrahydrofurro[3,2-d]isoxazol-3-yl)benzoate.

Workup

  1. washit is washed with 1 N hydrochloric acid and sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationIt is filtered with suction
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c362d2bf14374c32be33ed3c806b564c
Source dataset
uspto-grants-2004_03
Patent number
US06703348B2

Reaction notes

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