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

HRID 1841286Notes

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-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%).

Workup

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

Sources & evidence

ORD record: ord-98d20eddcae74c04a638268d77bf094a
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683111B2

Reaction notes

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