Sodium Bicarbonate → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one
Reaction equation
[OH:1][C:2]1(C#N)[CH2:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11][C:10]([CH3:17])=[CH:9][CH2:8][CH2:7][C:6]([CH3:18])=[CH:5][CH:4]=[C:3]1[CH:19]([CH3:21])[CH3:20].C(=O)([O-])O.[Na+]>C(OCC)C>[CH3:21][CH:19]([C:3]1[C:2](=[O:1])[CH2:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11][C:10]([CH3:17])=[CH:9][CH2:8][CH2:7][C:6]([CH3:18])=[CH:5][CH:4]=1)[CH3:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the cyanohydrin which is 1-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraenecarbonitrile (78.0 mg, 0.25 mmol) in ethyl ether (4 ml) is added to a saturated aqueous sodium hydrogen carbonate solution (2 ml) on an ice-water bath and the mixture is stirred for 10 minutes under nitrogen atmosphere. After confirming disappearance of the starting compound, the organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting residue is subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate=7:1) to give the desired ketone, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene -1-on (58.0 mg, 75%).