Tetrahydrofuran → Methyl 2-(4-aminomethylphenyl)-2-methylpropionate

HRID 1282117Notes

Reaction equation

HRID 1282117 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 18423002Methyl 2-(4-azidomethylphenyl)-2-methylpropionate

Product 1

HCID 18423094Methyl 2-(4-aminomethylphenyl)-2-methylpropionateYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 2-(4-azidomethylphenyl)-2-methylpropionate (48.1 g)and triphenylphosphine (59.5 g) in a mixed solvent of tetrahydrofuran (480 ml) and water (24 ml) was refluxed for 30 min. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=10:1, chloroform:methanol:aqueous ammonia=10:1:0.3) to give the title compound (29.4 g) as a pale-yellow oil.

Workup

  1. customThe solvent was evaporated
  2. customthe obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=10:1, chloroform:methanol:aqueous ammonia=10:1:0.3)

Sources & evidence

ORD record
ord-e1e5902d689740869b94c8493756d9eb
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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