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

HRID 1275733ノート

反応式

HRID 1275733 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 126958751-Methyl-9H-fluoren-9-one収率 16%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b04f891989034682814b78d4fa4fe186
出典データセット
uspto-grants-2000_12
特許番号
US06162824

反応ノート

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