Diethyl Ether → HCID 18361913, compound

HRID 382800Notes

Reaction equation

HRID 382800 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(OCC)C.[CH2:14]([C:16]1[C:30]([O:31][CH3:32])=[CH:29][C:19]2[C@@H:20]3[C@H:24]([CH2:25][C:26](=[O:27])[C:18]=2[C:17]=1[OH:33])[CH2:23][N:22]([CH3:28])[CH2:21]3)[CH3:15]>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:14]([C:16]1[C:30]([O:31][CH3:32])=[CH:29][C:19]2[CH:20]3[CH:24]([CH2:25][C:26](=[O:27])[C:18]=2[C:17]=1[OH:33])[CH2:23][N:22]([CH3:28])[CH2:21]3)[CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 444972Fumaric AcidHCID 9838455HCID 9838455, compound

Product 1

HCID 18361913HCID 18361913, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

168 mg (1.45 mmol) of fumaric acid and 50 ml of diethyl ether were added while stirring to a solution of 0.4 g (1.45 mmol) of cis-7-ethyl-6-hydroxy-8-methoxy-2-methyl-1,2,3,3a,4,9b-hexahydro-benzo[e]isoindol-5-one in 0.5 ml of ethanol. The mixture was stirred at room temperature for a further 17 hours and the solid was subsequently filtered off. 0.55 g (97%) of 7-ethyl-6-hydroxy-8-methoxy-2-methyl-1,2,3,3a,4,9b-hexahydro-benzo[e]isoindol-5-one fumarate (1:1) was obtained as a white solid with m.p. 195°.

Workup

  1. filtrationthe solid was subsequently filtered off

Sources & evidence

ORD record
ord-1b90bf70365d42f08509b5895c42cda8
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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