Trimethylsulfonium iodide → 2-tert-Butyl-2-(3-phenoxypropyl)oxirane

HRID 1649623ノート

反応式

HRID 1649623 の反応式
[CH3:1][C:2]([CH3:16])([C:4](=[O:15])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:3].[I-].[CH3:18][S+](C)C>O1CCCC1>[CH3:3][C:2]([C:4]1([CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:18][O:15]1)([CH3:16])[CH3:1]

参加物

4

反応物 2

HCID 75127Trimethylsulfonium iodideHCID 14076005HCID 14076005、化合物

生成物 1

HCID 140760082-tert-Butyl-2-(3-phenoxypropyl)oxirane収率 81.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

9 g (41 mMol) of 2,2-dimethyl-6-phenoxy-hexan-3-one are added dropwise to a mixture of 5.5 g (49 mMol) of potassium tert.-butylate in 40 ml of tetrahydrofuran at room temperature, with stirring, whereupon a clear yellowish solution forms. 12.5 g (61.5 mMol) of trimethylsulphonium iodide are then added and the mixture is stirred at 20° to 25° C. for 12 hours. Thereafter, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue which remains is taken up in methylene chloride and the resulting solution is washed three times with water. After the organic phase has been dried, the solvent is stripped off. 7.8 g (81% of theory) of 2-(1,1-dimethyl-ethyl)-2-(3-phenoxypropyl)-oxirane are obtained in this manner in the form of a liquid of refractive index nD20 =1.503. ##STR13##

後処理

  1. stirringthe mixture is stirred at 20° to 25° C. for 12 hours
  2. filtrationThereafter, the reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. washthe resulting solution is washed three times with water
  5. customAfter the organic phase has been dried

出典と根拠

ORDレコード
ord-52414ab9ff7e44d991e53980e3f41227
出典データセット
uspto-grants-1990_05
特許番号
US04921529

反応ノート

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