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

HRID 440220
Notes
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Reaction equation

HRID 440220 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 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

1
HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

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

  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-62651b3f8d364f57a1810c34580df975
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05518995

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes