Water → ethyl 5,10-dihydro-3-ethoxycarbonyl-1-methyl-10-oxo-1H-[2]benzoxepino[4,3-b]pyrrole-2-acetate

HRID 325411Notes

Reaction equation

HRID 325411 reaction equation
Cl[CH2:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[C:5]([C:7]1[N:11]([CH3:12])[C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]=1[OH:24])=[O:6].[H-].[Na+].O>CN(C=O)C>[CH2:22]([O:21][C:19]([C:9]1[C:8]2[O:24][CH2:2][C:3]3[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=3[C:5](=[O:6])[C:7]=2[N:11]([CH3:12])[C:10]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 135721047Ethyl 5-[o-(chloromethyl)benzoyl]-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

Product 1

HCID 20464719ethyl 5,10-dihydro-3-ethoxycarbonyl-1-methyl-10-oxo-1H-[2]benzoxepino[4,3-b]pyrrole-2-acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-[o-(chloromethyl)benzoyl]-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate (525 mg, 1.29 mmol) is suspended in 5 ml dry DMF under nitrogen followed by subsequent addition of sodium hydride (68 mg, 1.42 mmol, 50% dispersion in oil). Gas is evolved and the reaction turns dark brown. The mixture is stirred for one hour, then the solution is poured into water (50 ml). Upon agitation, a solid separates which is filtered and dried. The crude material is recrystallized from ethanol to give 426 mg (90%) of ethyl 5,10-dihydro-3-ethoxycarbonyl-1-methyl-10-oxo-1H-[2]benzoxepino[4,3-b]pyrrole-2-acetate.

Workup

  1. filtrationUpon agitation, a solid separates which is filtered
  2. customdried
  3. customThe crude material is recrystallized from ethanol

Sources & evidence

ORD record
ord-85ec5311d16746038d3e5433096efb33
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

Loading…