Veratrole → 3-Ethyl-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

HRID 460356

反応式

HRID 460356 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[C:11](O)(=[O:16])[CH2:12][CH:13]=[CH:14][CH3:15]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[O:9][CH3:10])[C:11](=[O:16])[CH2:12][CH:13]2[CH2:14][CH3:15]

参加物

3

反応物 2

HCID 7043Veratrole2 回HCID 212633-Pentenoic acid2 回

生成物 1

HCID 184456823-Ethyl-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

反応条件

温度
60 °C

実験手順

A mixture of 1,2-dimethoxy-benzene (Compound 47a) (21.9 mL, 0.170 mole) and pent-3-enoic acid (Compound 47b) (25.5 g, 0.255 mole) was stirred under argon in an ice bath. Polyphosphoric acid (230 g, 1.05 mole) was added slowly. After addition was complete, the ice bath was removed and the reaction heated for 16 hours at 60° C. The reaction was added to ice water and extracted with dichloromethane. The organic extracts were washed with 3N NaOH, water, brine and dried over Na2SO4. The solvent was then removed in vacuo to yield a red oil containing the crude title compound. The crude material was purified on a silica gel column using dichloromethane as eluent. The pure fractions were combined and concentrated to yield the racemic mixture of the title compound as an off-white solid. MS m/z 221 (M+H)+;

後処理

  1. additionAfter addition
  2. customthe ice bath was removed
  3. additionThe reaction was added to ice water
  4. extractionextracted with dichloromethane
  5. washThe organic extracts were washed with 3N NaOH, water, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was then removed in vacuo
  8. customto yield a red oil

出典と根拠

ORDレコード
ord-334eb78f38bc447596de491e97bd0020
出典データセット
uspto-grants-2007_03
特許番号
US07196110B2

関連ノート

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