Methanol → 1-Azido-3-phenylpropan-2-ol

HRID 1901678Notes

Reaction equation

HRID 1901678 reaction equation
[O:1]1[CH2:10][CH:2]1[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:11]=[N+:12]=[N-:13].[Na+].C(OC)=O.CO>O>[C:4]1([CH2:3][CH:2]([OH:1])[CH2:10][N:11]=[N+:12]=[N-:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 948262-(Phenylmethyl)oxirane

Product 1

HCID 137648321-Azido-3-phenylpropan-2-olYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 5 g of (±)-(2,3-epoxypropyl)benzene, 12.1 g of sodium azide, 60 ml of methyl formate and 270 ml of an 8:1 by volume mixture of methanol and water were used, to give 6.03 g of the title compound as a colorless oil having an Rf value of 0.3 (on silica gel thin layer chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 12

Sources & evidence

ORD record
ord-e16746bc14314472b859c2c29b2239bf
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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