Epibromohydrin → 2-[2-(4-Phenylbutyl)phenoxymethyl]oxirane

HRID 743170ノート

反応式

HRID 743170 の反応式
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(C1OC1)Br>CC(N(C)C)=O>[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH2:3][CH:2]2[CH2:5][O:4]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 18430EpibromohydrinHCID 125964892-(4-Phenylbutyl)phenolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 104931782-[2-(4-Phenylbutyl)phenoxymethyl]oxirane収率 99.8%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

7.84 g of potassium t-butoxide were added at room temperature to a solution of 15.81 g of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3) in 350 ml of dimethylacetamide, and the resulting mixture was stirred at the same temperature for 20 minutes, after which 11.46 ml of epibromohydrin were added to it. The mixture was then stirred at room temperature overnight, after which the reaction mixture was partitioned between water and ethyl acetate. The organic layer was then washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 7:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 19.68 g (yield 99.8%) of the title compound as a colorless oil.

後処理

  1. stirringThe mixture was then stirred at room temperature overnight
  2. customafter which the reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was then washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-1a2b1c091b15445bbd17f731e6876280
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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