Pyridine → Benzoic acid, acetylmethyl ester

HRID 31586

반응식

HRID 31586 반응식
N1C=CC=CC=1.C1COCC1.[OH:12][CH2:13][C:14](=[O:16])[CH3:15].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:17]([O:12][CH2:13][C:14](=[O:16])[CH3:15])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8299Hydroxyacetone

생성물 1

HCID 23137Benzoic acid, acetylmethyl ester수율 87.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a pyridine (25 ml) and THF (10 ml) solution of hydroxyacetone (5 g, 67.5 mmol), benzoyl chloride (12 ml, 103 mmol) was added dropwise at 0° C. in a nitrogen atmosphere and the mixture was stirred for 43 hours at room temperature. Ice was added to the reaction mixture, which was then diluted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient). Desired fractions were concentrated to obtain the title compound (10.56 g, 87.8% yield) as a light yellow oil.

후처리

  1. additionIce was added to the reaction mixture, which
  2. washThe organic layer was washed with 1N hydrochloric acid, water
  3. dry with materiala saline solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient)
  7. concentrationDesired fractions were concentrated

출처 및 근거

ORD 기록
ord-dd0a4ec0dabe404984930a4985ccb38e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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