Ethanol → 2-Ethyl-3a,4,5,9b-tetrahydro-6,7-dimethoxy-1H-benz[e]isoindole-1,3(2H)-dione

HRID 2290905Notes

Reaction equation

HRID 2290905 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][CH:12]3[CH:8]([C:9](=[O:17])[NH:10][C:11]3=[O:16])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:18][CH3:19].[CH2:20](O)[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:20]([N:10]1[C:9](=[O:17])[CH:8]2[CH:12]([CH2:13][CH2:14][C:15]3[C:3]([O:2][CH3:1])=[C:4]([O:18][CH3:19])[CH:5]=[CH:6][C:7]=32)[C:11]1=[O:16])[CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13746004HCID 13746004, compound

Product 1

HCID 137460052-Ethyl-3a,4,5,9b-tetrahydro-6,7-dimethoxy-1H-benz[e]isoindole-1,3(2H)-dioneYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of thee compound of example 3 (1.5 g, 5.8 mmole), absolute ethanol (0.42 mL, 7.3 mmole), triphenylphosphine (1.5 g, 5.8 mmole), and dry THF (9.8 mL) was stirred under N2 at 15° C. as diethyl azodicarboxylate (0.92 mL, 5.8 mmole) was added dropwise. The reaction mixture was stirred at room temperature for 18 hrs., then the crude reaction mixture was chromatographed on silica gel, eluting with CH2Cl2 containing 0.5% EtOH to obtain 0.96 g yellow solid (57%); M+ 289.

Workup

  1. additionwas added dropwise
  2. custom, then the crude reaction mixture
  3. customwas chromatographed on silica gel
  4. washeluting with CH2Cl2 containing 0.5% EtOH

Sources & evidence

ORD record
ord-69988db09b32421daf50c1bfba789066
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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