Water → (RS)-2-(2-buten-1-yl)-4-chloro-1-indanone

HRID 264475

反応式

HRID 264475 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[CH3:12][CH:13](O)[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:12]([CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[C:6]1=[O:11])[CH:13]=[CH:14][CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 113326814-chloro-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 54255457(RS)-2-(2-buten-1-yl)-4-chloro-1-indanone収率 81%

試薬・触媒・溶媒 1

HCID 64952,2-Dimethoxypropane溶媒

実験手順

A solution of 14.0 g of 4-chloro-1-indanone, 17.3 ml of 3-buten-2-ol and 140 mg of p-toluenesulfonic acid in 140 ml of 2,2-dimethoxy-propane was boiled under reflux for 64 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 6:1). 15.2 g (81%) of (RS)-2-(2-buten-1-yl)-4-chloro-1-indanone were obtained as a yellow oil.

後処理

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 6:1)

出典と根拠

ORDレコード
ord-06c3edcbae244e33b17d212c078e45c6
出典データセット
uspto-grants-1997_07
特許番号
US05646173

関連ノート

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