Diethyl Oxalate → HCID 11096938、化合物

HRID 1724737ノート

反応式

HRID 1724737 の反応式
[CH2:1]([CH2:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:21])[C:16](OCC)=[O:17])[CH3:13].CC[O-].[Na+]>>[CH2:12]([O:14][C:15](=[O:21])[C:16](=[O:17])[CH2:10][C:9](=[O:11])[CH2:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:13]

参加物

4

反応物 3

HCID 7268Diethyl OxalateHCID 17355Benzyl acetoneHCID 2723922Sodium ethoxide

生成物 1

HCID 11096938HCID 11096938、化合物収率 43.9%

実験手順

Benzylacetone (1.0 g, 6.75 mmol) and diethyloxalate (0.92 mL, 6.75 mmol) were mixed together, and then added to a solution of NaOEt (˜3 M, 2.3 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 19. The crude material was purified with 1:1 Hexanes: CH2Cl2 to obtain 0.7348 g (43.9%) of 19. 1H (CD3OD, 400 MHz): δ 7.27-7.12 (5H, m), 4.26 (2H, q, J=7.2Hz), 2.89 (2H, t, J=7.3 Hz), 2.81 (2H, t, J=7.3 Hz), 1.30 (3H, t, J=7.1 Hz) ppm. Partial 13C (CD3OD, 100 MHz): δ 163.32, 141.74, 129.43, 129.29, 127.16, 126.95, 103.06, 63.34, 43.46, 31.34, 14.24 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 14.24; CH2 carbons: 63.34, 43.46, 31.34; CH carbons: 129.43, 129.29, 127.16, 103.06 ppm. HPLC: 10.279 min.

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 19
  10. customThe crude material was purified with 1:1 Hexanes

出典と根拠

ORDレコード
ord-ad4fe852d3fd4f7cb6439a820c250d78
出典データセット
uspto-grants-2009_02
特許番号
US07488747B2

反応ノート

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