Diethyl Oxalate → HCID 11096938, 화합물

HRID 1366883노트

반응식

HRID 1366883 반응식
[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]

참가 물질

4

반응물 3

HCID 7268Diethyl OxalateHCID 17355Benzyl acetoneHCID 2723922Sodium ethoxide

생성물 1

HCID 11096938HCID 11096938, 화합물수율 43.9%

실험 절차

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=7.2 Hz), 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.

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

출처 및 근거

ORD 기록
ord-68cc4d56bdce4e8abdf5131e61602ae4
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893098B2

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