Sodium hydride → Ethyl 5-methyl-2-heptenoate

HRID 722843노트

반응식

HRID 722843 반응식
[H-].[Na+].C[CH:4]([CH2:8][CH3:9])[CH2:5][CH:6]=[O:7]>CCCCCC.C(COC)OC.COCC>[CH3:4][CH:9]([CH2:5][CH3:6])[CH2:8][CH:4]=[CH:5][C:6]([O:7][CH2:9][CH3:8])=[O:7]

참가 물질

6

반응물 2

HCID 24758Sodium hydrideHCID 275233-Methylvaleraldehyde

생성물 1

HCID 53937332Ethyl 5-methyl-2-heptenoate수율 122%

시약·촉매·용매 3

HCID 8058Hexane용매HCID 80711,2-Dimethoxyethane용매HCID 10903Methoxyethane용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% dispersion, 2.4 g, 65 mmol) was washed with hexane and suspended in dimethoxyethane 60 mL. While cooling in ice water bath triethyl phosphonoacetate was slowly added, calcd. 5 minutes. The reaction was stirred for 15 minutes at 0° C. and a solution of 3-methyl-1-pentanal 11 (6.5 g, 65 mmol) in methoxyethane 20 mL was added. After refluxing overnight, it was concentrated, water and hexane were added, the organic phase was separated, and the aqueous portion discarded. The solution was washed twice with brine and dried on magnesium sulfate. The solvent was evaporated to give 12 (6.75 g, 61%). 1H-NMR (CDCl3) δ 6.89 (m, 1H, —CH2CH:CHCOOEt), 5.77 (d, 1H, —CH2CH:CH:CHCOOEt), 4.16 (q, 2H, —COOCH2CH3), 2.15 and 1.98 (1H each and a multiplet, —CH2CH:CHCOOEt), 1.48 (m, 1H, C2H5(CH3)CHCH2), 1.30–1.10 (m), and 0.83.

후처리

  1. additionwas slowly added
  2. custom5 minutes
  3. temperatureAfter refluxing overnight
  4. concentrationit was concentrated
  5. additionwater and hexane were added
  6. customthe organic phase was separated
  7. washThe solution was washed twice with brine
  8. customdried on magnesium sulfate
  9. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-2d01f35aadee4ef1ace51dc0548772d1
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138542B2

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