Methanol → HCID 21474718, compound

HRID 1901706Notes

Reaction equation

HRID 1901706 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]2[CH2:14][O:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:15]=[N+:16]=[N-:17].[Na+].CO.C(OC)=O>O>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]([OH:13])[CH2:14][N:15]=[N+:16]=[N-:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 15580338HCID 15580338, compound

Product 1

HCID 21474718HCID 21474718, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 5.77 g of 3-phenylpropoxymethyloxirane (prepared as described in Preparation 52), 9.75 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 6.6 g of the title compound as a pale yellow oil having an Rf value of 0.27 (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-c27fdf5a617b4e89acc3ade7d7fb5573
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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