3-Methyl-2-butanone → Ethyl 3,4-dimethyl-2-pentenoate

HRID 1702960ノート

反応式

HRID 1702960 の反応式
[CH3:1][C:2]([CH:7]([CH3:9])[CH3:8])=[CH:3][C:4](Cl)=[O:5].C[CH:11](C)[C:12](=[O:14])C.[H-].[Na+]>COCCOCCOC>[CH3:1][C:2]([CH:7]([CH3:9])[CH3:8])=[CH:3][C:4]([O:14][CH2:12][CH3:11])=[O:5]

参加物

5

反応物 3

HCID 112513-Methyl-2-butanone3 回HCID 24758Sodium hydrideHCID 541273923,4-Dimethyl-2-pentenoylchloride

生成物 1

HCID 281491Ethyl 3,4-dimethyl-2-pentenoate

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

The 3,4-dimethyl-2-pentenoyl chloride (IX) utilized in the procedures of the present invention may be readily prepared from 3-methyl-2-butanone (XII) utilizing the Wittig reaction. In this procedure triethylphosphonoacetate is added to a suspension of sodium hydride in diglyme in an inert atmosphere at a temperature of between -10° C. and 5° C., suitably about 0° C. The mixture is stirred, suitably for about half an hour, to ensure formation of the Wittig reagent and the ketone (XII) added slowly thereto. There is utilized approximately 100% molar excess of the triethylphosphonoacetate with respect to the ketone (XII). The reaction is completed by allowing the reaction mixture to equilibrate with room temperature after completion of the addition, and remaining at ambient temperature from between 2 to 5 hours. The mixture is then recooled and carefully quenched with a large excess of water and the reaction product extracted therefrom with a reaction inert water insoluble organic solvent, suitably ether and the thus produced ethyl 3,4-dimethyl-2-pentenoate (XI) isolated from the ethereal extract in the usual manner.

後処理

  1. customthe Wittig reaction
  2. customto equilibrate with room temperature
  3. additionafter completion of the addition
  4. customremaining at ambient temperature from between 2 to 5 hours
  5. customcarefully quenched with a large excess of water
  6. extractionthe reaction product extracted

出典と根拠

ORDレコード
ord-93180cd20a444a6c88f437daa5b01c16
出典データセット
uspto-grants-1982_09
特許番号
US04350638

反応ノート

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