Acetic Acid → 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7848

반응식

HRID 7848 반응식
[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[CH3:14])[C:6]1=O)[CH2:2][CH2:3][CH3:4].C(O)(=O)C.N1CCCC1>C1(C)C=CC=CC=1.CCOCC>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:22])[CH:21]=[C:6]1[C:7]1[C:12](=[C:11]([CH3:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 219908922-Butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone

생성물 1

HCID 219908849a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one수율 55.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

A solution of impure 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone (0.96 g, 3.17 mmol), acetic acid (0.182 mL, 3.18 mmol) and pyrrolidine (0.265 mL, 3.18 mmol) in anhydrous toluene (15.9 mL) was stirred and heated in an oil bath at 80° C. for 16 hours. After cooling, the reaction mixture was diluted with Et2O (100 mL), washed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to a dark brown oil (0.86 g). The crude product was purified by chromatography on a Biotage FLASH 40S column, eluting with 9:1 hexanes-EtOAc, to afford 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.50 g) as an off-white solid.

후처리

  1. temperatureAfter cooling
  2. washwashed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum to a dark brown oil (0.86 g)
  6. customThe crude product was purified by chromatography on a Biotage FLASH 40S column
  7. washeluting with 9:1 hexanes-EtOAc

출처 및 근거

ORD 기록
ord-c4d098d6e0c64655809c3a2af90167be
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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