Acetic Acid → 1-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone

HRID 1018800ノート

反応式

HRID 1018800 の反応式
Cl[Si](C)(C)C.O[C:7]1([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1.[I-].[Na+].C(O)(=O)C>C(#N)C.[Zn]>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]([CH3:15])([CH3:16])[CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 223904201-[4-(Hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

生成物 1

HCID 223904281-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone収率 68%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6342Acetonitrile溶媒2 回

実験手順

38.1 ml of chlorotrimethylsilane are added over 45 minutes to a solution of 40.45 g of 1-[4-(hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V′.1) and 56.21 g of sodium iodide in 230 ml of anhydrous acetonitrile. During the addition, the temperature is maintained between 35° C. and 40° C. After stirring for 2 hours, 40 ml of acetonitrile and 39.4 ml of acetic acid are added. Next, 29.4 g of finely powdered zinc are added portionwise with stirring and at room temperature. The mixture is refluxed with vigorous stirring for 4 hours. After cooling to room temperature, the reaction medium is filtered through Celite and then washed with saturated aqueous sodium bicarbonate solution. The organic phase is concentrated under reduced pressure and the oil obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture; yield=68%; m.p.=54° C.

後処理

  1. additionDuring the addition
  2. temperaturethe temperature is maintained between 35° C. and 40° C
  3. stirringwith stirring and at room temperature
  4. temperatureThe mixture is refluxed
  5. stirringwith vigorous stirring for 4 hours
  6. filtrationthe reaction medium is filtered through Celite
  7. washwashed with saturated aqueous sodium bicarbonate solution
  8. concentrationThe organic phase is concentrated under reduced pressure
  9. customthe oil obtained
  10. customis purified by chromatography on a column of silica gel
  11. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-8c7d06312a5f4e58894b2201f733aefc
出典データセット
uspto-grants-2002_11
特許番号
US06482986B1

反応ノート

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