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

HRID 1366880

反応式

HRID 1366880 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d714d815680642e5b45a0f6a4beec6d5
出典データセット
uspto-grants-2011_02
特許番号
US07893098B2

関連ノート

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