Hydrochloric Acid → 6-(1H-indol-5-yl)hex-5-ene-2,4-dione

HRID 1056816노트

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HRID 1056816 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[B]=O.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.B(OC(C)C)(OC(C)C)OC(C)C.C(N)CCC.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=[CH:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

참가 물질

9

반응물 7

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 21531Triisopropyl borateHCID 31261AcetylacetoneHCID 516892Sodium BicarbonateHCID 589040Indole-5-carboxaldehydeHCID 6327189Boron monoxide

생성물 1

HCID 867132156-(1H-indol-5-yl)hex-5-ene-2,4-dione수율 49.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매4회

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온도
70 °C

실험 절차

In a 300 mL pear-shaped evaporating flask equipped with a cooling tube were placed 15.5 mL of ethyl acetate, 15.9 mL (155 mmol) of 2,4-pentanedione, and 3.24 g (46.5 mmol) of boron oxide. To the mixture under stirring at 70° C., 4.50 g (31.0 mmol) of 1H-indole-5-carboxaldehyde and a solution of 7.2 mL (31 mmol) of triisopropyl borate in ethyl acetate (31 mL) were added dropwise. The mixture was stirred at 70° C. for 30 minutes and a solution of 3.68 mL (37.2 mmol) of n-butylamine in ethyl acetate (9.3 mL) was added dropwise. After being stirred at 85° C. for 1 hour, the mixture was cooled down to 50° C., and 3 N hydrochloric acid (22 mL) was added thereto. The mixture was stirred at the same temperature for 10 minutes and neutralized with a saturated sodium bicarbonate solution. The resulting solution was diluted with ethyl acetate, washed twice with saturated brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 70/30) and crystallization (ethyl acetate/hexane) to give 3.46 g (49% yield) of the title compound as a yellow powder with the following properties.

후처리

  1. customIn a 300 mL pear-shaped evaporating flask equipped with a cooling tube
  2. stirringThe mixture was stirred at 70° C. for 30 minutes
  3. stirringAfter being stirred at 85° C. for 1 hour
  4. temperaturethe mixture was cooled down to 50° C.
  5. stirringThe mixture was stirred at the same temperature for 10 minutes
  6. washwashed twice with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 70/30) and crystallization (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-c3f72629ed78486c96cba663076fa5aa
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399635B2

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