Water → HCID 54199470, compound

HRID 1607399Notes

Reaction equation

HRID 1607399 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)C(OCC)=O)[CH3:2].O.[Cl-].[Li+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 539773572-Cinnamyl-2-(1-naphthylmethyl)malonic acid diethyl ester

Product 1

HCID 54199470HCID 54199470, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.5 g of the malonic acid diethyl ester obtained in 10 ml of dimethyl sulfoxide and 0.3 ml of water was added 0.92 g of lithium chloride, and the mixture was heated for 4.5 hours at from 180° to 190° C. After cooling, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.85 g of 2-(1-naphthylmethyl)-5-phenyl-4-pentenoic acid ethyl ester as a yellow oil.

Workup

  1. temperaturethe mixture was heated for 4.5 hours at from 180° to 190° C
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17343d6ea8524c88bce7bed649647154
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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