Tin tetrachloride → 1-Methyl-9H-fluoren-9-one

HRID 1275733노트

반응식

HRID 1275733 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.O=S(Cl)Cl.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:3]2[C:14](=[O:16])[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]=2[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 24287Tin tetrachlorideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 43213212-(3-methylphenyl)benzoic Acid

생성물 1

HCID 126958751-Methyl-9H-fluoren-9-one수율 16%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1.32 g (6.2 mmol) of 3'-methyl-2-biphenylcarboxylic acid, 40 mL of CH2Cl2 and 0.70 mL (9.6 mmol) of SOCl2 was warmed to reflux for 2 h. The solution was cooled to room temperature and 1.10 mL (9.4 mmol) of SnCl4 was added dropwise with stirring. The dark brown homogenous mixture was stirred for 18 h, poured into 50 mL of cold saturated aqueous NaHCO3, and extracted with 2×50 mL of ether. The ether extracts were combined and washed with 30 mL of saturated NaHCO3 solution, 30 mL of H2 0 and 30 mL of brine, dried (MgSO4) and concentrated in vacuo. Chromatography over SiO2 (Biotage 40 S) using 1% EtOAc in hexanes provided 168 mg (16% yield) of 1-methyl-9-fluorenone (Ladd, D. L. et al., Synthesis and dopaminergic binding of 2-aryldopamine analogues: Phenethylamines, 3-benzazepines, and 9-(aminomethyl)fluorenes. J. Med. Chem. 1986, 29, 1904-1912).

후처리

  1. temperaturewas warmed
  2. temperatureto reflux for 2 h
  3. stirringThe dark brown homogenous mixture was stirred for 18 h
  4. extractionextracted with 2×50 mL of ether
  5. washwashed with 30 mL of saturated NaHCO3 solution, 30 mL of H2 0 and 30 mL of brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b04f891989034682814b78d4fa4fe186
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162824

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