Methanol → 2-Propanol, 1-azido-3-phenoxy-

HRID 2294298Notes

Reaction equation

HRID 2294298 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+].C(OC)=O.CO>O>[O:1]([CH2:8][CH:9]([OH:10])[CH2:11][N:12]=[N+:13]=[N-:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 31217Phenyl glycidyl etherHCID 33557Sodium Azide

Product 1

HCID 27939012-Propanol, 1-azido-3-phenoxy-Yield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 1.00 g of phenoxymethyloxirane, 1.94 g of sodium azide, 10 ml of methyl formate and 45 ml of an 8:1 by volume mixture of methanol and water were used, to give 1.30 g of the title compound as a pale yellow oil having an Rf value of 0.26 (on silica gel thin 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-38ca26e1b7ea4882b9b6941ed6218a01
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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