Ethyl cyanoacetate → (E)-Ethyl 2-Cyano-5-methyl-2-hexenoate

HRID 1285512ノート

反応式

HRID 1285512 の反応式
[CH:1](=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8].N1CCCCC1>C(O)(=O)C>[C:7](/[C:9](=[CH:1]\[CH2:2][CH:3]([CH3:5])[CH3:4])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8]

参加物

5

反応物 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 115523-Methylbutanal

生成物 1

HCID 11019475(E)-Ethyl 2-Cyano-5-methyl-2-hexenoate収率 77.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a mixture of 3.00 mL (28.0 mmoles) of isovaleraldehyde and 3.00 mL (28.1 mmoles) of ethyl cyanoacetate in 4.0 mL of glacial acetic acid was added a solution of 0.10 mL of piperidine in 1.0 mL of glacial acetic acid. This mixture was subsequently stirred at room temperature for 18 hours, after which the product was isolated by diluting the mixture with 50 mL of 10% aqueous sodium chloride and extraction with ether. The combined extracts were washed thoroughly with 50 mL portions of 10% aqueous NaCl, followed by washes with 50 mL of 1:1 (v/v) 1M aqueous NaOH:saturated brine and saturated brine. The organic extracts were then dried over anhydrous magnesium sulfate and subsequently filtered. Removal of the ether by evaporation at reduced pressure, followed by distillation, afforded 3.91 g (77% yield) of cyanoester 5: bp 78°-90° C. (bath temperature, 0.07 mm).

後処理

  1. customafter which the product was isolated
  2. additionby diluting the mixture
  3. extractionwith 50 mL of 10% aqueous sodium chloride and extraction with ether
  4. washThe combined extracts were washed thoroughly with 50 mL portions of 10% aqueous NaCl
  5. dry with materialThe organic extracts were then dried over anhydrous magnesium sulfate
  6. filtrationsubsequently filtered
  7. customRemoval of the ether
  8. customby evaporation at reduced pressure
  9. distillationfollowed by distillation

出典と根拠

ORDレコード
ord-69c6a0fb3c7149d2858d563b8d74befc
出典データセット
uspto-grants-1986_01
特許番号
US04567265

反応ノート

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