Water → (3E)-4-(5-acetoxy-3-methyl-1,3-pentadien-1-ylidene)3,5,5-trimethyl-2-cyclohexen-1-one
Reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH:5]=[C:6]=[C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][C:10](=[O:15])[CH:9]=[C:8]1[CH3:16].C(N([CH2:23][CH3:24])CC)C.CNC1(NC)C=CN=CC1.[OH2:35]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[C:23]([O:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH:5]=[C:6]=[C:7]1[C:12]([CH3:13])([CH3:14])[CH2:11][C:10](=[O:15])[CH:9]=[C:8]1[CH3:16])(=[O:35])[CH3:24]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3E)-4-(5-hydroxy-3-methyl-1,3-pentadien-1-ylidene)-3,5,5-trimethyl-2-cyclohexen-1-one (1.2 g, 5.2 mmol) in acetic anydride (5.0 mL) and triethylamine (5.0 mL) cooled to 0° C., was added 4,4-dimethylaminopyridine (25 ng). After 15 min. water was added to the reaction mixture, and the product was extracted three times with ether. The combined ethereal extracts were washed with sodium chloride solution, and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography over silica gel in the manner described in Example 1 above gave the desired product (680 mg, 48%).
Workup
- extractionthe product was extracted three times with ether
- washThe combined ethereal extracts were washed with sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customEvaporation of the solvent and chromatography over silica gel in the manner
Sources & evidence
- ORD record
- ord-62651b3f8d364f57a1810c34580df975
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05518995
Reaction notes
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