Methanol → 3-(7-Phenylheptyloxy)-2-hydroxypropylazide

HRID 2294335Notes

Reaction equation

HRID 2294335 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]2[CH2:18][O:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:19]=[N+:20]=[N-:21].[Na+].C(OC)=O.CO>O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([OH:17])[CH2:18][N:19]=[N+:20]=[N-:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 214747647-Phenylheptyloxymethyloxirane

Product 1

HCID 214747743-(7-Phenylheptyloxy)-2-hydroxypropylazideYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 1.1 g of 7-phenylheptyloxymethyloxirane (prepared as described in Preparation 67), 1.4 g of sodium azide, 15 ml of methyl formate and 60 ml of an 8:1 by volume mixture of methanol and water were used, to give 1.27 g of the title compound having an Rf value of 0.45 (on silica gel thin layer chromatography, using a 1:3 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-c55afc14347e47d8a5834bcda4cae2d4
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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