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

HRID 323595Notes

Reaction equation

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]

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-00bcb7cb9c7d42348e232166408edd2f
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214820B1

Reaction notes

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