Potassium Carbonate → (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

HRID 1186034Notes

Reaction equation

Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5]Cl.[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][C:19]1[CH:26]=[C:25]([OH:27])[C:24]([OH:28])=[CH:23][C:20]=1[C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:17]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:7])[N:9]1[CH2:18][C:19]1[C:20]([C:21]#[N:22])=[CH:23][C:24]2[O:28][CH2:5][CH:4]=[CH:3][CH2:2][O:27][C:25]=2[CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

cis-1,4-Dichloro-2-butene (0.200 g, 1.6 mmol), 2((1,3-dioxoisoindolin-2-yl)methyl)-4,5-dihydroxybenzonitrile (0.500 g, 1.7 mmol), and potassium carbonate (0.77 g, 5.6 mmol) were suspended in dry DMF (80 ml) and heated to 50° C. for 5 h. The resulting mixture was cooled to room temperature and stirred overnight, then filtered. The filtrate was diluted with ethyl acetate, washed with water (2×), brine (2×), dried (Na2SO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with ethyl acetate/heptanes (50:50) to yield (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile as a residue. 1H NMR (CDCl3): δ 7.94-7.86 (m, 2H), 7.78-7.73 (m, 2H), 7.32 (s, 1H), 6.83 (s, 1H), 5.92-5.85 (m, 2H), 4.98 (s, 4H), 4.80 (s, 2H).

Workup

temperatureThe resulting mixture was cooled to room temperature
filtrationfiltered
additionThe filtrate was diluted with ethyl acetate
washwashed with water (2×), brine (2×)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was chromatographed
washeluting with ethyl acetate/heptanes (50:50)

Sources & evidence

ORD record: ord-b65fedcadacf4917979dffc016930505
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673890B2

Reaction notes

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