Oxalyl chloride → 4-cyclohexyl-N-(1,1-dimethylethyl)-N-hydroxy-cyclohexane-carboxamide
Reaction equation
[CH:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:23][C:24]([NH:27][OH:28])([CH3:26])[CH3:25]>O1CCCC1.CN(C)C=O.[OH-].[Na+]>[CH:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([C:13]([N:27]([C:24]([CH3:26])([CH3:25])[CH3:23])[OH:28])=[O:15])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 4-cyclohexyl-cyclohexanecarboxylic acid (1.47 g, 7 mmol) in 20 ml of tetrahydrofuran was added oxalyl chloride (0.67 ml, 7.7 mmol) and a few drops of dimethylformamide. After stirring for one hour, the reaction mixture was added dropwise into a cold (~0° C.), stirred solution of N-(1,1-dimethylethyl)hydroxylamine hydrochloride (1.75 g, 14 mmol) in 40 ml of 1N sodium hydroxide. The mixture was stirred for two hours, from 0° C. to room temperature and extracted three times with ethyl acetate. The combined ethyl acetate extracts were then washed twice with water, dried with anhydrous sodium sulfate and concentrated. Purification by flash chromatography provided 0.186 g of the 4-cyclohexyl-N-(1,1-dimethylethyl)-N-hydroxy-cyclohexane-carboxamide as a white solid (m.p. 119°-120° C.).
Workup
- additionthe reaction mixture was added dropwise into a cold (~0° C.)
- stirringThe mixture was stirred for two hours, from 0° C. to room temperature
- extractionextracted three times with ethyl acetate
- washThe combined ethyl acetate extracts were then washed twice with water
- dry with materialdried with anhydrous sodium sulfate
- concentrationconcentrated
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-81dccbcadc124a5a82208d0bc9af450a
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889874
Reaction notes
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