Acetone → HCID 18689379、化合物

HRID 1871841ノート

反応式

HRID 1871841 の反応式
[CH3:1][C:2]([CH3:4])=O.[C-]#N.[K+].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14].[C:19](=[O:22])([O-])O.[Na+].C([N:26](CC)CC)C>O.C(OCC)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:13]2[O:14][C:2]([CH3:4])([CH3:1])[C:19](=[O:22])[N:26]=2)[CH:16]=[CH:17][CH:18]=1

参加物

8

反応物 5

HCID 180AcetoneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 74374m-Anisoyl chlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 18689379HCID 18689379、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

50 mmol acetone is added at 0° C. to a solution of 57 mmol potassium cyanide in 50 ml water. 57 mmol 3-methoxybenzoyl chloride is added dropwise within 90 minutes at room temperature while stirring vigorously. After stirring for a further 90 min at 0° C. it is allowed to stand for 10 h at room temperature. It is admixed with 100 ml diethyl ether and the mixture was shaken out twice with 50 ml saturated sodium hydrogen carbonate solution each time and then with 100 ml water. The organic phase is separated and dried over sodium sulfate. The solvent is removed by distillation. The oily residue (6.6 g 3-methoxybenzoic acid-2'-cyanoisopropyl ester) is dried in a high vacuum and subsequently introduced into a mixture of 52 ml acetanhydride containing 10.4 ml 35% aqueous tetrafluoroboric acid. It is heated for 1 hour to boiling under reflux and after cooling to room temperature it is admixed with 300 ml ether. The precipitate that forms is suspended in 70 ml toluene. 70 mmol triethylamine is added to the suspension and it is stirred for 1 hour at room temperature. It is filtered. The filtrate is concentrated to dryness in a vacuum. The oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:1).

後処理

  1. stirringAfter stirring for a further 90 min at 0° C. it
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed by distillation
  5. dry with materialThe oily residue (6.6 g 3-methoxybenzoic acid-2'-cyanoisopropyl ester) is dried in a high vacuum
  6. additionsubsequently introduced into a mixture of 52 ml acetanhydride containing 10.4 ml 35% aqueous tetrafluoroboric acid
  7. temperatureIt is heated for 1 hour
  8. temperatureunder reflux
  9. stirringis stirred for 1 hour at room temperature
  10. filtrationIt is filtered
  11. concentrationThe filtrate is concentrated to dryness in a vacuum
  12. customThe oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:1)

出典と根拠

ORDレコード
ord-0d7bf7447c2d42e5aed1bf55436f6c4b
出典データセット
uspto-grants-2000_08
特許番号
US06107036

反応ノート

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