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Lithium Chloride → 2-(1-Naphthylmethyl)-6-phenylhexanoic acid ethyl ester

HRID 1607384
Notes
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Reaction equation

HRID 1607384 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]([CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C(OCC)=O)[CH3:2].[Cl-].[Li+]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 13727089Diethyl [(naphthalen-1-yl)methyl](4-phenylbutyl)propanedioate

Product 1

HCID 137270902-(1-Naphthylmethyl)-6-phenylhexanoic acid ethyl esterYield 89.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2.76 g of 2-(1-naphthylmethyl)-2-(4-phenylbutyl)malonic acid diethyl ester in 20 ml of dimethyl sulfoxide and 0.5 ml of water was added 1.27 g of lithium chloride, and then the mixture was heated for 8 hours at from 180° to 190° C. After cooling, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.06 g of 2-(1-naphthylmethyl)-6-phenylhexanoic acid ethyl ester as a light brown oil.

Workup

  1. temperaturethe mixture was heated for 8 hours at from 180° to 190° C
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic 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-9147948a0b5a44249172436c9d54e9b4
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04863904

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes