Water → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)-1-(2-azidoethyl)benzene

HRID 440470Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:14][CH:13]=1)(=O)=O.O>CN(C)C=O>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[O:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:1]=[N+:2]=[N-:3])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium azide (1.73 g, 26.61 mmol) was added to a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl methanesulfonate (5.24 g, 15.95 mmol) in N,N-dimethylformamide (50 ml). The mixture was stirred at 100° C. for 1 hour. Water (40 ml) was added to the reaction mixture. The mixture was extracted with ethyl ether and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=20/1) to give the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)-1-(2-azidoethyl)benzene (4.30 g, 98%).

Workup

extractionThe mixture was extracted with ethyl ether
dry with materialdried over magnesium sulfate
customAfter evaporation of the solvent
customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=20/1)

Sources & evidence

ORD record: ord-2d6c76b35f954b02b91e61826a908cff
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05519139

Reaction notes

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