Pentanoic Acid → HCID 22913316, compound

HRID 1377378Notes

Reaction equation

HRID 1377378 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28])=[CH:20][N:19]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:32](O)(=[O:37])[CH2:33][CH2:34][CH2:35][CH3:36].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35][CH3:36])[C:27]([F:30])([F:28])[F:29])=[CH:20][N:19]=3)=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 22913400HCID 22913400, compound

Product 1

HCID 22913316HCID 22913316, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 2-(4'-pentylbiphenyl-4-yl)-5-(2-hydroxy-3,3,3-trifluoropropoxy)-pyrimidine (80 mg), pentanoic acid (20 mg), DCC (50 mg), DMAP (10 mg) and methylene chloride (10 ml) was stirred at room temperature, followed by filtering off deposited solids, concentrating the mother liquid, purifying the residue by means of silica gel column chromatography and recrystalizing from ethanol to obtain the objective 2-(4'-pentylbiphenyl-4-yl)-5-(2-pentanoyloxy-3,3,3-trifluoropropoxy)-pyrimidine (90 mg). Cr 33° C. mesophase 84° C. iso

Workup

  1. filtrationby filtering off
  2. concentrationconcentrating the mother liquid
  3. custompurifying the residue by means of silica gel column chromatography
  4. customrecrystalizing from ethanol

Sources & evidence

ORD record
ord-1d2a91efb67445148918f0610ef7b127
Source dataset
uspto-grants-1997_09
Patent number
US05665270

Reaction notes

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