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

HRID 1285512노트

반응식

HRID 1285512 반응식
[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]

참가 물질

5

반응물 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 115523-Methylbutanal

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-69c6a0fb3c7149d2858d563b8d74befc
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04567265

반응 노트

불러오는 중…