Water → 2-Aminomethyl-5-benzyloxy-pyran-4-one

Reaction equation

[N:1]([CH2:4][C:5]1[O:6][CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[O:6][CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1

Participants

Procedure

To a stirred solution of 2-azidomethyl-5-benzyloxy-pyran-4-one (4) (30.0 g, 116.7 mmol) in tetrahydrofuran (500 mL) were added triphenyl phosphine (61.16 g, 233.46 mmol) and water (5.2 mL) and the mixture was refluxed for 16 h. After completion of the reaction, solvent was evaporated under reduced pressure, then it was purified by normal column chromatography to get (2-aminomethyl-5-benzyloxy-pyran-4-one (5) (13.0 g, 48.16%) as a brown solid.