1-Methylimidazole → 1-O-(p-toluenesulfonyl)-2-methylene-1,3-propanediol

HRID 2187354

反応式

HRID 2187354 の反応式
[CH2:1]=[C:2]([CH2:5][OH:6])[CH2:3][OH:4].C([Sn](=O)CCCC)CCC.CN1C=CN=C1.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>C1(C)C=CC=CC=1.O>[C:29]1([CH3:30])[CH:31]=[CH:32][C:26]([S:23]([O:4][CH2:3][C:2](=[CH2:1])[CH2:5][OH:6])(=[O:25])=[O:24])=[CH:27][CH:28]=1

参加物

7

反応物 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 61221Dibutyltin oxideHCID 770481,3-Propanediol, 2-methylene-

生成物 1

HCID 184754641-O-(p-toluenesulfonyl)-2-methylene-1,3-propanediol収率 32.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

2-Methylene-1,3-propanediol (480 mg) and dibutyltinoxide (1,7 g) were dissolved in toluene (30 ml) and the resulting suspension was refluxed for 1 hour eliminating water with the help of a Dean-Stark apparatus. The flask was cooled down to room temperature and then, N-methyl-imidazol (797 ml) and tosyl chloride (1,56 g) were added. After 15 minutes stirring, the reaction crude was directly purified by column chromatography (hexane-ethyl acetate v/v from 7:1 to 1:1). The title compound (428 mg) was obtained as a white solid.

後処理

  1. temperaturethe resulting suspension was refluxed for 1 hour
  2. customthe reaction crude
  3. customwas directly purified by column chromatography (hexane-ethyl acetate v/v from 7:1 to 1:1)

出典と根拠

ORDレコード
ord-79d8c75fdd72464a9b13680a82011c96
出典データセット
uspto-grants-2002_06
特許番号
US06410528B1

関連ノート

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