Tetrahydrofuran → t-Butyl [3-(aminomethyl)phenoxy]acetate

Reaction equation

[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+]=[N-].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[C:13]([O:12][C:10](=[O:11])[CH2:9][O:8][C:7]1[CH:17]=[CH:18][CH:19]=[C:5]([CH2:4][NH2:1])[CH:6]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

Procedure

To a mixed liquid of 5.16 g of t-butyl [3-(azidomethyl)phenoxy]acetate and 50 ml of THF were added 6.17 g of triphenylphosphine and 1.04 ml of water, followed by stirring at room temperature for 4 days. The solvent was evaporated and diisopropyl ether was added thereto. The precipitated solid was separated by filtration and the solvent was evaporated again. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol-saturated aqueous ammonia) to obtain 4.10 g of t-butyl[3-(aminomethyl)phenoxy]acetate as a pale yellow oily substance.