Water → 1-Phenyl-7-oxabicyclo[4.1.0]heptane

HRID 1108006

反応式

HRID 1108006 の反応式
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=[O:14].[Na+].OOS([O-])=O.[K+].O>C(#N)C.O>[C:1]1([C:7]23[O:14][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 962WaterHCID 130431-PhenylcyclohexeneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 1001931-Phenyl-7-oxabicyclo[4.1.0]heptane収率 83%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of phenyl cyclohexene (79 mg, 0.5 mmol) in a mixture of acetonitrile (4.5 ml) and water (2 drops) were added first finely crushed NaHCO3 (168 mg, 2 mmol) and oxone (307 mg, 0.5 mmol) then the catalyst (0.05 mmol). The resulting yellow suspension was allowed to react at RT, under good stirring. TLC was used to follow the reaction which indicated that the reaction was finished in 2 h. Water (3 ml) was added to the reaction mixture followed by extraction into methylene dichloride. The organic extracts were combined and dried over anhydrous sodium sulphate. Concentration on a rotary evaporator gave a material which was purified on a column using 2% ethyl acetate:petrol mixture as eluent to give the desired compound as a colourless oil. (72 mg, 83% yield, 70% e.e).

後処理

  1. customto react at RT, under good stirring
  2. customthe reaction which
  3. extractionfollowed by extraction into methylene dichloride
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationConcentration
  6. customon a rotary evaporator
  7. customgave a material which
  8. customwas purified on a column

出典と根拠

ORDレコード
ord-94395df33f7f4c38bcdf1e38099dd4be
出典データセット
uspto-grants-2000_05
特許番号
US06063920

関連ノート

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