Potassium Carbonate → 2-((4-Vinylnaphthalen-1-yl)methyl)isoindoline-1,3-dione

HRID 1503731Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)C(=O)[N:3]1[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15][CH:14]=1.[C:25]([O-:28])([O-])=O.[K+].[K+].O1CCOC[CH2:32]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:23]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:25]2=[O:28])=[CH:14][CH:15]=1)=[CH2:32]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 4-((1,3-dioxoisoindolin-2-yl)methyl)-1-naphthaldehyde (9 g, 28.5 mmol) in 1,4-dioxane (100 mL) were added K2CO3 (6 g, 42.8 mmol) and methyl triphenyl phosphonium bromide (15.3 g, 35.7 mmol) at ambient temperature. The reaction mixture was heated at 100° C. for 14 h and then was cooled to ambient temperature. The reaction mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 20% EtOAc in petroleum ether) afforded the title compound as a white solid (6 g, 67%): mp 146-147° C.; 1H NMR (400 MHz, CDCl3) δ 8.35 (m, 2H), 7.95 (m, 4H), 7.65 (m, 4H), 7.39 (m, 1H), 5.81 (m, 1H), 5.45 (m, 1H), 5.21 (s, 2H); ESIMS m/z 314.13 ([M+H]+).

Workup

temperaturewas cooled to ambient temperature
filtrationThe reaction mixture was filtered
concentrationthe obtained filtrate was concentrated under reduced pressure
customPurification by flash chromatography (SiO2, 100-200 mesh; 20% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-0fc7d697f1e043cc9d8e1bd5064789d2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212164B2

Reaction notes

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