Water → 1-[2-(4-Allyloxy-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 33488Notes

Reaction equation

HRID 33488 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Cl)=[CH:9][CH:8]=1)[CH:4]=[CH2:5].[N:15]1([CH2:20][CH2:21][OH:22])[CH:19]=[CH:18][N:17]=[N:16]1.O>CN(C)C=O>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:22][CH2:21][CH2:20][N:15]2[CH:19]=[CH:18][N:17]=[N:16]2)=[CH:9][CH:8]=1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 123479361-Allyloxy-4-chloromethyl-benzene

Product 1

HCID 236145301-[2-(4-Allyloxy-benzyloxy)-ethyl]-1H-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

197 mg (8.21 mmol) 95% sodium hydride were given at −50° C. to a solution of 1.00 g (5.47 mmol) 1-allyloxy-4-chloromethyl-benzene and 619 mg (5.47 mmol) 2-(1H-[1,2,3]-triazol-1-yl)-ethanol in 9.0 ml N,N-dimethylformamide (DMF). The mixture was allowed to warm slowly to room temperature (r.t.), stirred overnight and 10 ml water was added. The formed oil was collected with 10 ml dichloromethane, the aqueous phase extracted with 10 ml dichloromethane and the combined organic phases dried over Na2SO4.

Workup

  1. customThe formed oil was collected with 10 ml dichloromethane
  2. extractionthe aqueous phase extracted with 10 ml dichloromethane
  3. dry with materialthe combined organic phases dried over Na2SO4

Sources & evidence

ORD record
ord-5bb210cf415341438fbb5281da5cc019
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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