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

HRID 345720ノート

反応式

HRID 345720 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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##

後処理

  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)

出典と根拠

ORDレコード
ord-c52b7aaa13914af0ba5b691d39001cd0
出典データセット
uspto-grants-1991_10
特許番号
US05059340

反応ノート

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