Dicyclohexylcarbodiimide → (S)-5-(6'-methyloctanoyloxy)-2-(4'-propylbiphenyl-4-yl)pyrimidine

HRID 345720Notes

Reaction equation

HRID 345720 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH3:23][C@@H:24]([CH2:32][CH3:33])[CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:23][C@@H:24]([CH2:32][CH3:33])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[N:4][CH:3]=1)=[O:30]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5312346(S)-6-methyloctanoic acidHCID 199911075-Hydroxy-2(4'-propyl-biphenyl-4-yl)pyrimidine

Product 1

HCID 18647434(S)-5-(6'-methyloctanoyloxy)-2-(4'-propylbiphenyl-4-yl)pyrimidineYield 67.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Hydroxy-2(4'-propyl-biphenyl-4-yl)pyrimidine (10 g, 0.034 mol) was dissolved in dichloromethane (100 ml), followed by adding (S)-6-methyloctanoic acid (7.9 g, 0.05 mol), DCC (20.6 g, 0.1 mol) and DMAP (3.3 g), agitating the mixture at room temperature for 2 hours, filtering off deposited crystals, washing the filtrate with 6N-HCl, then with 2N-NaOH and further with water until the washing water became neutral, drying the organic layer over anhydrous magnesium sulfate, distilling off dichloromethane and recrystallizing the residue from ethanol (150 ml) to obtain (S)-5-(6'-methyloctanoyloxy)-2-(4'-propylbiphenyl-4-yl)pyrimidine (9.9 g). This product was a liquid crystal and exhibited the following phase transition points (see also Table 1): ##STR88##

Workup

  1. filtrationfiltering off
  2. washwashing the filtrate with 6N-HCl
  3. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  4. distillationdistilling off dichloromethane
  5. customrecrystallizing the residue from ethanol (150 ml)

Sources & evidence

ORD record
ord-c52b7aaa13914af0ba5b691d39001cd0
Source dataset
uspto-grants-1991_10
Patent number
US05059340

Reaction notes

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