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

HRID 1067867ノート

反応式

HRID 1067867 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) 67 7.10-7.35 (m, 10H); 6.85 (d, 2H); 6.06 (t, 1H); 4.27 (q, 2H); 4.07 (m, 3H); 3.68 (m, 1H); 3.45 (m, 1H); 3.17 (bs, 4 H); 3.06 (d, 2H); 2.69 (q, 2H); 1.27 (t, 3H); 0.99 (t, 3H).

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-9762251db6b14e77a10d0c436c3f46fb
出典データセット
uspto-grants-2001_06
特許番号
US06248781B1

反応ノート

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