Hexanoic Acid → HCID 20087318, compound

HRID 275220Notes

Reaction equation

HRID 275220 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[CH:29][N:28]=2)=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19][CH3:20].[C:40](O)(=[O:46])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.ClCCl>[C:40]([O:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2[CH:31]=[N:32][C:27]([C:24]3[CH:23]=[CH:22][C:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=3)=[N:28][CH:29]=2)=[CH:38][CH:37]=1)(=[O:46])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 20087288HCID 20087288, compound

Product 1

HCID 20087318HCID 20087318, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.8 g of N,N'-dicyclohexylcarbodiimide is added within 5 minutes while stirring to a solution of 1.0 g of 4-(2-[4-pentylphenyl]-5pyrimidinyl)phenol, 0.4 g of caproic acid and 0.05 g of 4-(dimethylamino)pyridine in 30 ml of dichloro-methane. The reaction mixture is stirred overnight, then filtered, the filtrate is washed with saturated sodium bicarbonate solution and with water and concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the fractions which are pure according to thin-layer chromatography give 1.0g of 4-(2-[4-pentylphenyl]-5-pyrimidinyl)phenyl hexanoate; m.p. (C-SC) 124° C., phase transition (SC -SA) 185° C., cl.p. (SA -I) 224° C.

Workup

  1. filtrationfiltered
  2. washthe filtrate is washed with saturated sodium bicarbonate solution and with water
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the fractions which

Sources & evidence

ORD record
ord-e3e1e29b3a484c40891fd218d003755c
Source dataset
uspto-grants-1995_02
Patent number
US05393458

Reaction notes

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