Diethyl Oxalate → 8-methyl-2,4-dioxoNonanoic acid ethyl ester

HRID 1724734

반응식

HRID 1724734 반응식
[CH3:1][CH:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[CH2:10]([O:12][C:13](=[O:19])[C:14](OCC)=[O:15])[CH3:11].CC[O-].[Na+]>>[CH2:10]([O:12][C:13](=[O:19])[C:14](=[O:15])[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH:2]([CH3:9])[CH3:1])[CH3:11]

참가 물질

4

반응물 3

HCID 7268Diethyl OxalateHCID 135726-Methyl-2-heptanoneHCID 2723922Sodium ethoxide

생성물 1

HCID 574350738-methyl-2,4-dioxoNonanoic acid ethyl ester수율 46.9%

실험 절차

6-Methyl-2-heptanone (0.9981 g, 7.80 mmol) and diethyloxalate (1.06 mL, 7.80 mmol) were mixed together, and then added to a solution of NaOEt (˜3 M, 2.6 mL) stirring in an ice bath under N2. After stirring for 15 minutes, the reaction was warmed to room temperature and stirred overnight. The reaction was quenched at 0° C. with 1N HCl and extracted 2× with CH2Cl2. The combined organics were washed with H2O, dried with Na2SO4, filtered, and concentrated to yield crude 16. The crude material was purified with 1:1 Hexanes: CH2Cl2 to obtain 0.8342 g (46.9%) of 16. 1H (CD3OD, 400 MHz): δ 6.36 (1H, s), 4.30 (2H, q, J=7.1 Hz), 2.50 (2H, t, J=7.3 Hz), 1.68-1.59 (2H, m), 1.61-1.50 (1H, m), 1.33 (3H, t, J=7.1 Hz), 1.25-1.17 (2H, m), 0.89 (6H, d, J=7.0 Hz) ppm. 13C (CD3OD, 100 MHz): δ 204.41, 166.93, 163.28, 102.66, 63.29, 41.89, 39.41, 28.92, 23.65, 22.89, 14.33 ppm.

후처리

  1. stirringAfter stirring for 15 minutes
  2. stirringstirred overnight
  3. customThe reaction was quenched at 0° C. with 1N HCl
  4. extractionextracted 2× with CH2Cl2
  5. washThe combined organics were washed with H2O
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield crude 16
  10. customThe crude material was purified with 1:1 Hexanes

출처 및 근거

ORD 기록
ord-3dd601b34e3141c080c970a90c182e35
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488747B2

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