Cyclohexanepropanoic acid → 2-(4-Octyloxyphenyl)pyrimidin-5-yl 3-cyclohexylpropionate

HRID 1489830Notes

Reaction equation

HRID 1489830 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH:23]1([CH2:29][CH2:30][C:31](O)=[O:32])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[CH:23]1([CH2:29][CH2:30][C:31]([O:1][C:2]2[CH:3]=[N:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=3)=[N:6][CH:7]=2)=[O:32])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 69702Cyclohexanepropanoic acidHCID 144963952-(4-(Octyloxy)phenyl)pyrimidin-5-ol

Product 1

HCID 229026862-(4-Octyloxyphenyl)pyrimidin-5-yl 3-cyclohexylpropionateYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.00 g (10.0 mmol) of 5-hydroxy-2-(4-octyloxyphenyl)pyrimidin, 1.56 g (10.0 mmol) of 3-cyclohexylpropionic acid, 2.06 g (10.0 mmol) of N,N-dicyclohexylcarbodiimide and 0.1 g of 4-N,N-dimethylaminopyridine in 80 ml of dichloromethane are stirred at room temperature for 18 hours. Insoluble constituents are then filtered off, the mixture is evaporated, and the residue is purified by chromatography (silica gel/dichloromethane) and recrystallization from hexane, giving 2.52 g of 2-(4-octyloxyphenyl)pyrimidin-5-yl 3-cyclohexylpropionate. ##STR12##

Workup

  1. filtrationInsoluble constituents are then filtered off
  2. customthe mixture is evaporated
  3. customthe residue is purified by chromatography (silica gel/dichloromethane) and recrystallization from hexane

Sources & evidence

ORD record
ord-3476c79d55264a95b808e5735d453337
Source dataset
uspto-grants-1997_10
Patent number
US05679792

Reaction notes

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