2-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone → 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7856

반응식

HRID 7856 반응식
[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[Cl:14])[C:6]1=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.Cl.CCOC(C)=O>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:23])[C:21]([CH3:22])=[C:6]1[C:7]1[C:12](=[C:11]([Cl:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 1

HCID 219909112-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone

생성물 1

HCID 219908769a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one수율 60.6%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A solution of 2-butyl-4-chloro-5-methoxy-2-(3-oxo-pentyl)-1-indanone (250 mg, 0.74 mmol) in acetic acid (2 mL) was diluted with 6N aqueous HCl (2 mL). The resulting mixture was stirred and heated in an oil bath at 90° C. for 18 hours, then kept at room temperature for 2 days. The mixture was diluted with EtOAc (20 mL), washed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (250 mg). The crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (143 mg).

후처리

  1. washwashed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to an oil (250 mg)
  5. customThe crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates

출처 및 근거

ORD 기록
ord-6121252028114c99b582eb81c90945f8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

연결된 노트

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