Benzoyl chloride → 4-(Furan-2-yl)-2,6-dimethoxyphenyl benzoate

HRID 56539노트

반응식

HRID 56539 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=1.CCN(CC)CC.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:24]([O:14][C:9]1[C:8]([O:15][CH3:16])=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:11][C:10]=1[O:12][CH3:13])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 543508354-(Furan-2-yl)-2,6-dimethoxyphenol

생성물 1

HCID 584319964-(Furan-2-yl)-2,6-dimethoxyphenyl benzoate수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-(furan-2-yl)-2,6-dimethoxyphenol (1.3 g, 5.9 mmol) in anhydr CH2Cl2 (20 mL) under argon was added Et3N (1.6 mL, 11.5 mmol) then the mixture was cooled over an ice bath. Benzoyl chloride (0.75 mL, 6.4 mmol) was added dropwise and the reaction was stirred for 3 hrs. 10% aqueous NaHCO3 and CH2Cl2 were added, stirred, and the layers were separated. The organics were washed with H2O and saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. Purification by chromatography (0-25% EtOAc-hexanes) gave 4-(furan-2-yl)-2,6-dimethoxyphenyl benzoate as a light yellow solid (0.54 g isolated from chromatography of approximately half of the crude product; 57% yield).

후처리

  1. temperaturethe mixture was cooled over an ice bath
  2. stirringstirred
  3. customthe layers were separated
  4. washThe organics were washed with H2O and saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (0-25% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-5add161b8f0e4ac89eb3c1944c095e46
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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