Benzyl Bromide → 2,4-Pentanedione, 3-benzyl-

HRID 1064543

반응식

HRID 1064543 반응식
[O-]CC.[Na+].[H-].[Na+].[CH3:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([CH:9]([C:8](=[O:13])[CH3:7])[C:10](=[O:12])[CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 2723922Sodium ethoxide

생성물 1

HCID 977572,4-Pentanedione, 3-benzyl-수율 82.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of sodium ethoxide (freshly prepared from sodium hydride (0.474 g, 19.8 mmol) and anhydrous ethanol (50 mL)) was added pentane-2,4-dione (6.00 g, 60.0 mmol). The resulting mixture was heated to 50° C. while a solution of benzyl bromide (3.42 g, 20 mmol) in ethanol (20 mL) was added over 30 minutes. The reaction was then heated to reflux. After 2 hours, the mixture was concentrated, and the residue was dissolved in ethyl acetate, washed three times with water, once with brine, dried (magnesium sulfate) and concentrated to afford an oil. Flash chromatography over silica (ethyl acetate/dichloromethane) afforded 3.13 g (82%) of a colorless oil. The proton spectrum showed the product exists as equal parts of the keto and enol tautomers: 1H NMR (CDCl3) δ 16.81 (s, 0.5H), 7.13-7.32 (m, 5H), 4.00 (t, J=7.6 Hz, 0.5H), 3.65 (s, 1H), 3.14 (d, J=7.6 Hz, 0.5H), 2.06-2.13 (m, 6H) ppm.

후처리

  1. additionwas added over 30 minutes
  2. temperatureThe reaction was then heated to reflux
  3. concentrationthe mixture was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed three times with water
  6. dry with materialonce with brine, dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customto afford an oil

출처 및 근거

ORD 기록
ord-84fe8a4ccbc646d5980c678b6cdc7eeb
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969728B2

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