p-Toluenesulfonic acid → (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone

HRID 264434

反応式

HRID 264434 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH3:13][CH:14](O)[CH:15]=[CH2:16].COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:13]([CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[CH:14]=[CH:15][CH3:16]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 117163-Buten-2-olHCID 3340366-Methoxy-1-Indanone

生成物 1

HCID 54031441(RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone収率 55%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 20.0 g of 6-methoxy-1-indanone, 31.3 ml of 3-buten-2-ol, 53.5 ml of 2,2-dimethoxypropane and 200 mg of p-toluenesulfonic acid in 200 ml of toluene was brought to boiling. The resulting methanol/acetone mixture was distilled off and the reaction solution was subsequently boiled under reflux overnight. After cooling, the solution was washed with 50 ml of saturated sodium hydrogen carbonate solution. The aqueous washing was extracted with 50 ml of ethyl acetate, the organic phases were combined, dried with magnesium sulfate and evaporated in a vacuum. Purification on silica gel (hexane/diethyl ether 5:1) yielded 13.6 g (55%) of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone as a pale yellow oil.

後処理

  1. distillationThe resulting methanol/acetone mixture was distilled off
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. washthe solution was washed with 50 ml of saturated sodium hydrogen carbonate solution
  5. washThe aqueous washing
  6. extractionwas extracted with 50 ml of ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. customevaporated in a vacuum
  9. customPurification on silica gel (hexane/diethyl ether 5:1)

出典と根拠

ORDレコード
ord-e1496153e2bd4337af31d50f11c970cb
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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