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

HRID 394640ノート

反応式

HRID 394640 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-5H-dibenzo[a,d]cyclohepten (5.0 g, 15.2 mmol), ethyl 3-(4-hydroxyphenyl)-2-ethoxypropanoate (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 were separated. The organic phase was dried and the solvent evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with benzene/chloroform, to give first 2.5 g of 5-propenylidene-10,11-dihydro-5H-dibenzo(a,d)cyclohepten and then 1.5 g (21%) of the title compound as an oil. 1H NMR (250 MHz, CDCl3) δ7.10-7.35 (m, 10 H); 6.85 (d, 2 H); 6.06 (t, 1 H); 4.27 (q, 2 H); 4.07 (m, 3 H); 3.68 (m, 1 H); 3.45 (m, 1 H); 3.17 (bs, 4 H); 3.06 (d, 2 H); 2.69 (q, 2 H); 1.27 (t, 3 H); 0.99 (t, 3 H).

後処理

  1. customthe phases were separated
  2. customThe organic phase was dried
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel eluting with benzene/chloroform

出典と根拠

ORDレコード
ord-87f8f108f5c84f54bf6d9689b9f4cf36
出典データセット
uspto-grants-2003_08
特許番号
US06602901B2

反応ノート

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