Dicyclohexylcarbodiimide → 4-(5-Undecyl-pyrimidin-2-yl)phenyl 3-ethyl-1-cyclopentene-1-carboxylate

HRID 1826557Notes

Reaction equation

HRID 1826557 reaction equation
[CH2:1]([C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:25]([CH:27]1[CH2:31][CH2:30][C:29]([C:32](O)=[O:33])=[CH:28]1)[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:25]([CH:27]1[CH2:31][CH2:30][C:29]([C:32]([O:24][C:21]2[CH:20]=[CH:19][C:18]([C:15]3[N:16]=[CH:17][C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:13][N:14]=3)=[CH:23][CH:22]=2)=[O:33])=[CH:28]1)[CH3:26]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 221342213-Ethyl-1-cyclopentene-1-carboxylic acidHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 155149784-(5-Undecyl-pyrimidin-2-yl)phenyl 3-ethyl-1-cyclopentene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.9 g of 4-(5-undecyl-pyrimidin-2-yl)phenol, 1.5 g of 3-ethyl-1-cyclopentene-1-carboxylic acid and 2.1 g of dicyclohexylcarbodiimide are stirred for 24 h in 50 ml of dichloromethane at room temperature. Filtration, removal of the dichloromethane by distillation, purification by chromatography (silica gel; dichloromethane/heptane) and recrystallization from acetonitrile affords the target compound.

Workup

  1. filtrationFiltration, removal of the dichloromethane
  2. distillationby distillation, purification
  3. customby chromatography (silica gel; dichloromethane/heptane) and recrystallization from acetonitrile
  4. customaffords the target compound

Sources & evidence

ORD record
ord-4322494066cc4a929d8fbfd18ddf3161
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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