2,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-one → HCID 86084843, compound

HRID 1522715Notes

Reaction equation

[C:1]1([C:7]2[C:8](=O)C(C3C=CC=CC=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)=[CH:35][CH:34]=1)#[CH:32]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:32]2[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:31]=2[C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[CH:35][CH:34]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 210 °C

Procedure

A solution of 2,3,4,5-tetraphenylcyclopentadienone (4) (Morgenroth et al, Tetrahedron 1997, 53, 15349) (1.14 g, 2.96 mmol) and (3) (354 mg, 1.98 mmol) in diphenyl ether (3 mL) was deoxygenated and heated at 210° C. under argon for 3 hours. The reaction mixture was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:1) as eluent to give (5) (988 mg, 93%).

Workup

customThe reaction mixture was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:1) as eluent

Sources & evidence

ORD record: ord-c3bfd8237abe47018332ccbf1d30b030
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09078330B2

Reaction notes

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