Benzoyl chloride → 1,3,3a,4,6,6a-Hexahydrofuro[3,4-c]pyrrol-5-yl(phenyl)methanone

HRID 1283609Notes

Reaction equation

HRID 1283609 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]1[CH:14]2[CH2:15][NH:16][CH2:17][CH:13]2[CH2:12][O:11]1.[OH-].[Na+]>O>[C:1]([N:16]1[CH2:17][CH:13]2[CH2:12][O:11][CH2:10][CH:14]2[CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chloride2×HCID 14798Sodium HydroxideHCID 21421150Hexahydro-1H-furo[3,4-c]pyrrole2×

Product 1

HCID 418581,3,3a,4,6,6a-Hexahydrofuro[3,4-c]pyrrol-5-yl(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoyl chloride (14.06 grams, 0.1 mole), Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, was slowly added to a mixture of [compound (X)] hexahydro-1H-furo(3,4-c)pyrrole (11.3 grams, 0.1 mole) and sodium hydroxide (10 grams) in 300 ml of water at 10°C. After the addition of benzoyl chloride, the reaction mixture was stirred at room temperature for 2 to 3 hours and the product was extracted with diethyl ether (4 × 200 ml). Removal of the ether gave the product 5-benzoyl-hexahydro-1H-furo(3,4-c)pyrrole, represented by formula (XI), as a clear viscous liquid which solidified on standing. The product was crystallized from diethyl ether and had a melting point of 47° to 48°C.

Workup

  1. extractionthe product was extracted with diethyl ether (4 × 200 ml)
  2. customRemoval of the ether

Sources & evidence

ORD record
ord-4712f1c6743240b49b4643e661eb5f96
Source dataset
uspto-grants-1976_08
Patent number
US03975532

Reaction notes

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