Methanol → HCID 21474724, compound

HRID 1901703Notes

Reaction equation

HRID 1901703 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH:14]2[CH2:16][O:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:17]=[N+:18]=[N-:19].[Na+].CO.C(OC)=O>O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH:14]([OH:15])[CH2:16][N:17]=[N+:18]=[N-:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 21474728HCID 21474728, compound

Product 1

HCID 21474724HCID 21474724, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 4.0 g of 5-phenylpentyloxymethyloxirane (prepared as described in Preparation 49), 5.9 g of sodium azide, 160 ml of an 8:1 by volume mixture of methanol and water and 40 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 0.25 (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-fff2239922b04667862b7b867f0124ee
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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