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

HRID 33492Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[N:13]1([CH2:18][CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:17]=[CH:16][N:15]=[N:14]1.[H-].[Na+].O>CN(C)C=O.ClCCl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:19][CH2:18][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -30 °C

Procedure

1.58 g (6.14 mmol) (4-allyloxy-phenyl)-methanethiol and 1.64 g (6.14 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester were dissolved in 15 ml N,N-dimethylformamide (DMF) and cooled to −30° C. 294 mg (12.3 mmol) 95% Sodium hydride were added, the mixture allowed to warm to room temperature (r.t.) and stirred for 12 h. 10 ml Water were added and the residue dissolved in dichloromethane. The organic phase was dried over Na2SO4, solvents removed and the remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1) to yield 1.33 g (79%) yellow oil.

Workup

temperatureto warm to room temperature (r.t.)
dry with materialThe organic phase was dried over Na2SO4, solvents
customremoved
customthe remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1)

Sources & evidence

ORD record: ord-6a37d3286e9249aabfc0d2ce2d01f0fc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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