Dicyclohexylcarbodiimide → (S)-4-[4'-(2''-methylbutylcarbonyloxy)phenyl]-1-benzyloxybenzene

HRID 324156Notes

Reaction equation

HRID 324156 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C@@H:23]([CH2:28][CH3:29])[CH2:24][C:25](O)=[O:26].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:22][C@@H:23]([CH2:28][CH3:29])[CH2:24][C:25]([O:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[CH:20][CH:19]=1)=[O:26]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 642230(S)-3-methyl-pentanoic acidHCID 152688474-(4-Benzyloxyphenyl)phenol

Product 1

HCID 20645782(S)-4-[4'-(2''-methylbutylcarbonyloxy)phenyl]-1-benzyloxybenzeneYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{circle around (1)}: A mixture comprising 2.8 g of 4-(4′-benzyloxyphenyl)phenol, 1.2 g of (S)-2-methylbutylcarboxylic acid, 3.09 g of DCC and 15 g of dichloromethane was stirred at room temperature for 30 minutes. Then, a catalytic amount of 4-N,N-dimethylaminopyridine was added to the mixture, and the mixture was further stirred at room temperature for 12 hours. After finishing the reaction, insoluble substances were filtered off, followed by distilling off dichloromethane from the filtrate. The resultant residue was purified by means of silica gel column chromatography, whereby 3.5 g of (S)-4-[4′-(2″-methylbutylcarbonyloxy)phenyl]-1-benzyloxybenzene was obtained in the form of a colorless crystal.

Workup

  1. stirringthe mixture was further stirred at room temperature for 12 hours
  2. customthe reaction, insoluble substances
  3. filtrationwere filtered off
  4. distillationby distilling off dichloromethane from the filtrate
  5. customThe resultant residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-f7f6de8ed2ec4105a7df70badad5e3ab
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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