Lithium Hydroxide → 5-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid

HRID 1924993Notes

Reaction equation

HRID 1924993 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:10])[O:7][C:6]=1[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:4].[Li+].[OH-].C1COCC1>O>[Br:10][C:8]1[O:7][C:6]([CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 590231235-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid methyl ester

Product 1

HCID 590230235-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid methyl ester (643.8 mg, 1.82 mmol) and LiOH (115 mg, 2.74 mmol) in 1:1 THF:H2O (30 mL) is refluxed for 3 hours. The solvent is evaporated in vacuo to afford the title compound (620 mg, 99%) which is used in the next step without further purification.

Workup

  1. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-4a7b6472c0f04fb49e56d4b86e9da017
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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