2-Cyclohexen-1-one → 3-[Benzenesulfonyl-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclohexanone

HRID 602774Notes

Reaction equation

HRID 602774 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[O:12][C:13]([CH:16]3[CH2:18][CH2:17]3)=[N:14][N:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[C:20]1(=[O:26])[CH2:25][CH2:24][CH2:23][CH:22]=[CH:21]1>CO.[NH4+].[Cl-]>[C:1]1([S:7]([CH:10]([C:11]2[O:12][C:13]([CH:16]3[CH2:17][CH2:18]3)=[N:14][N:15]=2)[CH:22]2[CH2:23][CH2:24][CH2:25][C:20](=[O:26])[CH2:21]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 135942-Cyclohexen-1-oneHCID 5360545SodiumHCID 672669922-Benzenesulfonylmethyl-5-cyclopropyl-[1,3,4]oxadiazole

Product 1

HCID 672666653-[Benzenesulfonyl-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclohexanoneYield 44.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To 2.47 g (9.3 mmol) of 2-benzenesulfonylmethyl-5-cyclopropyl-[1,3,4]oxadiazole in 25 mL of MeOH at 0° C., 170 μL (0.93 mmol, 0.1 eq) of a solution of sodium methoxyde (5.4 M in MeOH) were added. After 15 min, 895 mg (9.3 mmol, 1 eq) of cyclohex-2-enone were added. The reaction mixture was stirred from 0° C. to RT over 4 hours, diluted with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 2:1 gave 1.48 g (44%) of 3-[benzenesulfonyl-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-methyl]-cyclohexanone as a racemic mixture of diastereomers, white solid, MS: 361 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2fd8e693abde4ba89db4df277adef7b2
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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