Water → HCID 68711735, 화합물

HRID 29337

반응식

HRID 29337 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]=[CH2:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].B.C1C[O:22]CC1.O.C([O-])([O-])=O.C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>C1COCC1>[OH:22][CH2:17][CH2:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 159762Sodium percarbonateHCID 2723981Borane;tetrahydrofuranHCID 68713160HCID 68713160, 화합물

생성물 1

HCID 68711735HCID 68711735, 화합물수율 80.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.35 g (1.5 mmol) of 3-methyl-4-vinyl-1-benzofuran-2-carboxylate (Example 87, Step 1) in 3 mL of THF, cooled in an ice bath, was added 1 mL (1 mmol) of borane-THF complex (1.0M solution in THF). The reaction was stirred at room temperature for 2 hours. The reaction was cooled in an ice bath and 1.5 mL of water was added. Next 0.61 g of sodium percarbonate was added in one portion. The reaction was heated at ˜50° C. for 1 hour, then cooled to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1) to provide 0.20 g of ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate. Yield 54%. m.p. 88-90° C.; MS 249.1 (M+H)+.

후처리

  1. temperatureThe reaction was cooled in an ice bath
  2. temperatureThe reaction was heated at ˜50° C. for 1 hour
  3. temperaturecooled to room temperature
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-965edae8814849798c651b63a638beac
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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