Sodium periodate → 4-Carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

HRID 29327

반응식

HRID 29327 반응식
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=C)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:19].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[C:9]2[C:12](=[C:16]=[O:19])[CH:13]=[CH:14][CH:15]=[C:8]2[O:7]1)=[O:5])[CH3:2]

참가 물질

7

반응물 2

HCID 23667635Sodium periodateHCID 687131603-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

생성물 1

HCID 865990284-Carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester수율 89.1%

시약·촉매·용매 4

HCID 6386tert-Butanol촉매HCID 30318Osmium Tetroxide촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To a solution of 0.250 g (1.087 mmol) of 3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester (Example 87, Step 1) in 7.5 mL of dioxane and 2.5 mL of water was added 0.272 mL of 2.5 weight % osmium tetroxide in t-butanol (0.022 mmol) and the reaction was stirred for 10 minutes at room temperature, turning yellow-brown in color. Sodium periodate (0.488 g, 2.282 mmol) was then added in several portions over 30 minutes and a white precipitate formed. The reaction was stirred at room temperature for 2 h and then diluted with water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.225 g of 4-carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

후처리

  1. customa white precipitate formed
  2. stirringThe reaction was stirred at room temperature for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

출처 및 근거

ORD 기록
ord-937225491e044952839ab9ba28439eeb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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