Lithium azide → Methyl 2-(4-azidomethyl-2-propylphenoxy)-2-phenylacetate

HRID 1645957Notes

Reaction equation

HRID 1645957 reaction equation
Br[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1.[N-:24]=[N+:25]=[N-:26].[Li+]>CS(C)=O>[N:24]([CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1)=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 19781781Methyl (4-bromomethyl-2-propylphenoxy)-2-phenylacetate

Product 1

HCID 19802747Methyl 2-(4-azidomethyl-2-propylphenoxy)-2-phenylacetateYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 45 mg (0.12 mmol) of the product from Step H in 0.37 ml of dry DMSO was added 7.3 mg (0.15 mmol) of lithium azide. The solution was stirred at room temperature under N2 for 4.5 hours. After flash chromatography on silica gel (elution with 10:1 hexane-EtOAc), 33 mg (83%) of the title compound was obtained as a gum; satisfactory purity by TLC in 4:1 hexane-EtOAc.

Sources & evidence

ORD record
ord-46f408de006b4d718edb1a475794698c
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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