Methanol → 3-(8-Phenyloctyloxy)-2-hydroxypropylazide

HRID 2294332

Reaction equation

HRID 2294332 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]2[CH2:19][O:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:20]=[N+:21]=[N-:22].[Na+].C(OC)=O.CO>O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]([OH:18])[CH2:19][N:20]=[N+:21]=[N-:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 214747108-Phenyloctyloxymethyloxirane

Product 1

HCID 214747133-(8-Phenyloctyloxy)-2-hydroxypropylazideYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 2.4 g of 8-phenyloctyloxymethyloxirane (prepared as described in Preparation 64), 2.97 g of sodium azide, 20 ml of methyl formate and 80 ml of an 8:1 by volume mixture of methanol and water were used, to give 2.7 g of the title compound having an Rf value of 0.29 (on silica gel thin layer chromatography, using a 1:5 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-0e72fa836a4a4791a92087d1a49e55af
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Linked notes

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