Methanol → 1-Azido-3-(benzyloxy)propan-2-ol

HRID 1901700Notes

Reaction equation

HRID 1901700 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[N-:15]=[N+:16]=[N-:17].[Na+].C(OC)=O>O>[CH2:1]([O:8][CH2:9][CH:10]([OH:11])[CH2:12][N:15]=[N+:16]=[N-:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 94247Benzyl glycidyl ether

Product 1

HCID 132105261-Azido-3-(benzyloxy)propan-2-olYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 4.92 g of benzyloxymethyloxirane (prepared as described in Preparation 46), 160 ml of an 8:1 by volume mixture of methanol and water, 9.75 g of sodium azide and 40 ml of methyl formate were used, to give 5.7 g of the title compound having an Rf value of 0.22 (on silica gel thin layer chromatography, using a 1:5 by volume mixture of ethyl acetate and hexane as the developing solvent) as a pale yellow oil.

Workup

  1. customA procedure similar to that described in Preparation 12

Sources & evidence

ORD record
ord-332a9202e8f4440bb5720bb66e8b0a4e
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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