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

HRID 1756017Notes

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 eluting9 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 eluting9 with n-hexane/ethyl acetate (=20/1)

Sources & evidence

ORD record: ord-c04255875ae14b1bb5ba28d97da59cf3
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05439911

Reaction notes

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