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

HRID 1060855노트

반응식

HRID 1060855 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d3f51b94aa443c28a73d4db4ae44131
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525086B2

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