Allyl Alcohol → 14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

HRID 486864

反応式

HRID 486864 の反応式
C(O)C=C.[Cl:5][CH2:6][C:7]([CH3:26])=[CH:8][CH2:9][CH2:10][C:11]([CH3:25])=[CH:12][CH2:13][CH2:14][C:15]([CH3:24])=[CH:16][CH:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][OH:20].[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[Cl:5][CH2:6][C:7]([CH3:26])=[CH:8][CH2:9][CH2:10][C:11]([CH3:25])=[CH:12][CH2:13][CH2:14][C:15]([CH3:24])=[CH:16][CH:17]=[C:18]([CH:21]([CH3:22])[CH3:23])[CH:19]=[O:20]

参加物

5

反応物 3

HCID 7858Allyl AlcoholHCID 3084030Barium manganateHCID 5368470314-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol

生成物 1

HCID 5388146714-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the allylalcohol which is 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol (492 mg, 1.51 mmol) in methylene chloride (22 ml) is added powdered barium manganate (8.5 g) and the mixture is vigorously stirred under argon atmosphere. After 8 hours, disappearance of the starting compound is confirmed and the reaction mixture is filtered and washed. The filtrate and the washing liquid are combined and concentrated. The resulting residue is purified by silica gel column chromatography (n-nexane/ethyl acetate=15:1) to give the desired 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (468 mg, 95%).

後処理

  1. filtrationthe reaction mixture is filtered
  2. washwashed
  3. concentrationconcentrated
  4. customThe resulting residue is purified by silica gel column chromatography (n-nexane/ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-17e3dc326e68418998b35e2f3b930b64
出典データセット
uspto-grants-1994_03
特許番号
US05292911

関連ノート

読み込み中…