Thionyl Chloride → 2-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one

HRID 1921844Notes

Reaction equation

HRID 1921844 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:4]([C:18]([OH:20])=O)[CH:3]=1.O=S(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[O:6][CH:5]2[CH2:7][N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:18](=[O:20])[CH:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 590230235-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid

Product 1

HCID 590230372-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-oneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid (618 mg, 1.82 mmol) and SOCl2 (0.136 mL) in DCM (2 mL) is stirred at 85° C. for 18 hours. The mixture is concentrated in vacuo and purified by silica gel column chromatography eluting with 7:3 petroleum ether:ethyl acetate to afford the title compound (0.169 g, 28%).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. custompurified by silica gel column chromatography
  3. washeluting with 7:3 petroleum ether

Sources & evidence

ORD record
ord-0f57974bffc446e495cf59f332fee80f
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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