Dimethylformamide → 5-Prop-2-en-1-ylidene-10,11-dihydro-5H-dibenzo(a,d)(7)annulene

HRID 275975ノート

反応式

HRID 275975 の反応式
S(O[CH2:6][CH2:7][CH:8]=[C:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=2)(C)(=O)=O.OC1C=CC(CC(OCC)C(OCC)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC=CC=1>[CH:8](=[C:9]1[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=2[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2)[CH:7]=[CH2:6]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 17127123-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl methanesulfonateHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

生成物 1

HCID 6160605-Prop-2-en-1-ylidene-10,11-dihydro-5H-dibenzo(a,d)(7)annulene収率 70.8%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-(3-mesyloxypropylidene)-10,11-dihydro-dibenzo[a,d]cycloheptene (5.0 g, 15.2 mmol), ethyl 3-(4-hydroxyphenyl)-2-ethoxypropionate (3.7 g, 15.5 mmol), potassium carbonate (2.9 g, 21 mmol) and dimethylformamide (10 ml) was heated at 100° C. for 5 h. Benzene (200 ml) and water (200 ml) were added and the phases separated. The organic phase was dried, the solvent evaporated, and the product purified by chromatography on silica gel (benzene/chloroform eluent) to give first 2.5 g of 5-propenylidene-10,11-dihydro-5H-dibenzo(a,d)cycloheptene and then the title compound as an oil; 1.5 g (21%).

後処理

  1. customthe phases separated
  2. customThe organic phase was dried
  3. customthe solvent evaporated
  4. customthe product purified by chromatography on silica gel (benzene/chloroform eluent)

出典と根拠

ORDレコード
ord-ad70f34aacf74bd2b5d9544ef7176828
出典データセット
uspto-grants-2002_03
特許番号
US06353018B1

反応ノート

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