1-Chloro-4-(chloromethyl)benzene → methyl (RS)-5-[3-(4-chlorobenzyloxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate

HRID 322870Notes

Reaction equation

HRID 322870 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:23])[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>CN(C)C=O>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][C:2]2[CH:3]=[C:4]([C:8](=[O:23])[CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 10805064methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate

Product 1

HCID 10812856methyl (RS)-5-[3-(4-chlorobenzyloxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of methyl (RS)-5-[3-(hydroxy)phenyl]-4-(2-methylphenyl)-5-oxo-pentanoate (1.68 g) in dimethylformamide (20 mL) is treated with 60% sodium hydride in oil (237 mg). After 15 minutes the mixture is treated with 4-chlorobenzyl chloride (953 mg) and heated at 60° C. for 1 hour. The reaction mixture is evaporated, the residue is dissolved in diethyl ether, washed with water, dried, and evaporated, to give methyl (RS)-5-[3-(4-chlorobenzyloxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate (2.05 g), in the form of a colouriess oil. [NMR(CDCl3):- 2.0-2.5(4H,m),2.5(3H,s), 3.65(3H,s), 4.8(1H,m),5.0(2H,q),7.0-7.5(12H)].

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in diethyl ether
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e42362c546ef4b9b81f715ec8f15cb7b
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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