Acetone → HCID 22282695, 화합물

HRID 2252749노트

반응식

HRID 2252749 반응식
[C:1]([C:4]1[C:12]2[C:7](=[C:8]3[CH2:15][CH2:14][O:13][C:9]3=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=O)[CH3:2].B.CC(C)=O>O1CCCC1>[CH2:1]([C:4]1[C:12]2[C:7](=[C:8]3[CH2:15][CH2:14][O:13][C:9]3=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 180AcetoneHCID 6331BoraneHCID 22282666HCID 22282666, 화합물

생성물 1

HCID 22282695HCID 22282695, 화합물수율 45.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred mixture of 3-acetyl-7,8-dihydrofuro[2,3-g]indole (721 mg, 3.58 mmol) in tetrahydrofuran (25 mL) under an atmosphere of Ar at ambient temperature was added, over 5 min, borane (1.0 M in THF; 18 mL, 18 mmol). The resultant mixture was stirred at ambient temperature for 30 min, then heated to reflux for 2 h before cooling to room temperature. Acetone (25 mL) was added and the mixture was heated to reflux for a further 30 min. The mixture was cooled to room temperature then all solvent was removed in vacuo. Methanol (40 mL) was added, and the mixture was again heated to reflux for 30 min, then cooled to room temperature followed by solvent removal in vacuo. Purification by flash column chromatography [SiO2; ethyl acetate-heptane (1:4)] afforded the product (302 mg, 45%) as a white solid: m.p. 91-92.5° C.; Found: C, 76.90; H, 7.02; N, 7.44%. C12H13NO requires: C, 76.98; H, 7.00; N, 7.48%.

후처리

  1. additionwas added, over 5 min
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. temperaturethe mixture was heated
  5. temperatureto reflux for a further 30 min
  6. temperatureThe mixture was cooled to room temperature
  7. customall solvent was removed in vacuo
  8. additionMethanol (40 mL) was added
  9. temperaturethe mixture was again heated
  10. temperatureto reflux for 30 min
  11. temperaturecooled to room temperature
  12. customfollowed by solvent removal in vacuo
  13. customPurification by flash column chromatography [SiO2; ethyl acetate-heptane (1:4)]

출처 및 근거

ORD 기록
ord-0bd3348b1e3942fcbea0d92a19f7d947
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323473B2

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