Dicyclohexylcarbodiimide → 5-benzyl-3-furyl-methyl (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

HRID 485707

反応式

HRID 485707 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:26])[C@@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([OH:25])=[O:24].[CH2:27]([C:34]1[O:38][CH:37]=[C:36]([CH2:39]O)[CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:16][C:17]1([CH3:26])[C@@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([O:25][CH2:39][C:36]1[CH:35]=[C:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:38][CH:37]=1)=[O:24]

参加物

6

反応条件

温度
0 °C

実験手順

4.06 g of dicyclohexylcarbodiimide were added at 0° C. to a solution of 1.52 g of (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane carboxylic acid in 40 ml of methylene chloride followed by addition of a few crystals of 4-dimethylaminopyridine and stirring at 0° C. for 15 minutes. A solution of 2.07 g of 5-benzyl-3-furyl-methanol in 10 ml of methylene chloride were added at 0° C. to the mixture which was stirred at 20° C. for 4 hours and was then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 1-1 benzene-petroleum ether (b.p.=35° to 70° C.) yielded 2.72 g of 5-benzyl-3-furyl-methyl (1R,cis)2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate.

後処理

  1. stirringwas stirred at 20° C. for 4 hours
  2. filtrationwas then filtered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 1-1 benzene-petroleum ether (b.p.=35° to 70° C.)

出典と根拠

ORDレコード
ord-304b9272d1af44d0abec985c17edaa23
出典データセット
uspto-grants-1985_08
特許番号
US04537897

関連ノート

読み込み中…