Dicyclohexylcarbodiimide → 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine

HRID 1728262ノート

反応式

HRID 1728262 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([OH:37])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18].[C:38](O)(=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([O:37][C:38](=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 5282715cis-beta-Octenoic acidHCID 190171892-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine

生成物 1

HCID 676342202-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine収率 83.7%

試薬・触媒・溶媒 2

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

実験手順

0.8 g of N,N'-dicyclohexylcarbodiimide was added within 5 minutes while stirring to a solution of 1.0 g of 2-[4-(5[propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine, 0.4 g of (Z)-3-octenoic acid and 0.05 g of 4-(dimethylamino)pyridine in 30 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered and the filtrate was 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 thin-layer chromatographically pure fractions gave 1.0 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine.

後処理

  1. filtrationfiltered
  2. washthe filtrate was 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 thin-layer chromatographically pure fractions

出典と根拠

ORDレコード
ord-40373b5c592c4b369fb23c202e4c595d
出典データセット
uspto-grants-1994_07
特許番号
US05326497

反応ノート

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