Water → (RS)-2-(2-buten-1-yl)-6-fluoro-1-indanone

HRID 264378

反応式

HRID 264378 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[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:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[C:8]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 15194646-Fluoro-1-indanone

生成物 1

HCID 54473173(RS)-2-(2-buten-1-yl)-6-fluoro-1-indanone収率 71%

試薬・触媒・溶媒 1

HCID 64952,2-Dimethoxypropane溶媒

実験手順

A solution of 19.7 g of 6-fluoro-1-indanone, 27.0 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 200 ml of 2,2-dimethoxypropane was boiled under reflux for 67 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 4:1). 18.9 g (71%) of (RS)-2-(2-buten-1-yl)-6-fluoro-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 4:1)

出典と根拠

ORDレコード
ord-fa51b04d2872429fa101b618a15410db
出典データセット
uspto-grants-1997_07
特許番号
US05646173

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