Phenylacetyl chloride → 5-phenylacetyl-hexahydro-1H-furo(3,4-c)pyrrole

HRID 1283608Notes

Reaction equation

HRID 1283608 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:12]1[CH:16]2[CH2:17][NH:18][CH2:19][CH:15]2[CH2:14][O:13]1.[OH-].[Na+]>>[C:1]1([CH2:7][C:8]([N:18]2[CH2:19][CH:15]3[CH2:14][O:13][CH2:12][CH:16]3[CH2:17]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 14798Sodium HydroxideHCID 21421149Hexahydro-1H-furo[3,4-c]pyrrole hydrochloride

Product 1

HCID 214211565-phenylacetyl-hexahydro-1H-furo(3,4-c)pyrroleYield 83.7%

Procedure

Phenylacetyl chloride (15.46 grams, 0.1 mole), Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, was slowly added to a mixture of hexahydro-1H-furo(3,4-c)pyrrole hydrochloride (14.96 grams, 0.1 mole) and 300 ml aqueous sodium hydroxide (10.0 grams, 0.25 mole NaOH in water) at 10°C. After the phenylacetyl chloride addition, the ice bath was removed and the reaction mixture was stirred for 1.5 hours. The reaction mixture was extracted with diethyl ether (4 × 200 ml) and the extract treated with DARCO G-60 (activated carbon). Removal of diethyl ether gave 5-phenylacetyl-hexahydro-1H-furo(3,4-c)pyrrole (19.35 grams) a clear viscous liquid which solidified on cooling. This product was recrystallized from diethyl ether and had a melting point of 47.5° to 48.5°C.

Workup

  1. customthe ice bath was removed
  2. extractionThe reaction mixture was extracted with diethyl ether (4 × 200 ml)
  3. additionthe extract treated with DARCO
  4. customRemoval of diethyl ether

Sources & evidence

ORD record
ord-12ff75bfe19b4902af74ddca212f064d
Source dataset
uspto-grants-1976_08
Patent number
US03975532

Reaction notes

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