Water → (3E)-4-(5-acetoxy-3-methyl-1,3-pentadien-1-ylidene)3,5,5-trimethyl-2-cyclohexen-1-one

HRID 1589990Notes

Reaction equation

HRID 1589990 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].CN[C:20]1(NC)[CH:25]=CN=CC1.[OH2:28]>C(OC(=O)C)(=O)C.C(N(CC)CC)C>[C:25]([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:28])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 22406474(3E)-4-(5-hydroxy-3-methyl-1,3-pentadien-1-ylidene)-3,5,5-trimethyl-2-cyclohexen-1-oneHCID 865890494,4-Dimethylaminopyridine

Product 1

HCID 22406473(3E)-4-(5-acetoxy-3-methyl-1,3-pentadien-1-ylidene)3,5,5-trimethyl-2-cyclohexen-1-oneYield 48%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8471TriethylamineSolvent

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 anhydride (5.0 mL) and triethylamine (5.0 mL) cooled to 0° C., was added 4,4-dimethylaminopyridine (25 n g). 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

  1. extractionthe product was extracted three times with ether
  2. washThe combined ethereal extracts were washed with sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and chromatography over silica gel in the manner

Sources & evidence

ORD record
ord-2e8077029553410eb0a3e5e4d14f081f
Source dataset
uspto-grants-1993_04
Patent number
US05201931

Reaction notes

Loading…