Methanol → HCID 21474785, compound

HRID 2294329Notes

Reaction equation

HRID 2294329 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]2[CH2:17][O:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:18]=[N+:19]=[N-:20].[Na+].CO.C(OC)=O>O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]([OH:16])[CH2:17][N:18]=[N+:19]=[N-:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 21474757HCID 21474757, compound

Product 1

HCID 21474785HCID 21474785, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 4 g of 6-phenylhexyloxymethyloxirane (prepared as described in Preparation 61), 5.5 g of sodium azide, 100 ml of an 8:1 by volume mixture of methanol and water and 25 ml of methyl formate were used, to give 4.5 g of the title compound as a pale yellow oil having an Rf value of 0.39 (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-4045771ed482402da372b308b186aaaf
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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