Hexanoic Acid → HCID 20087318, compound

HRID 1728257Notes

Reaction equation

HRID 1728257 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]-5-pyrimidinyl)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 1.0 g 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-3200179750c44a60bd9a999276c1e7eb
Source dataset
uspto-grants-1994_07
Patent number
US05326498

Reaction notes

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