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

HRID 33492ノート

反応式

HRID 33492 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22242087[4-(Prop-2-en-1-yloxy)phenyl]methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

生成物 1

HCID 222420761-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole収率 79%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6a37d3286e9249aabfc0d2ce2d01f0fc
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

反応ノート

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