Ethyl Acetate → 2-Methoxyfluoren-9-one

HRID 1089829ノート

反応式

HRID 1089829 の反応式
O[C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7]C=C[CH:10]=1)[CH:5]=2.[OH-:16].[Na+].[C:18]([O:21][CH2:22][CH3:23])(=O)C>C(Cl)Cl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH3:18][O:21][C:22]1[CH:23]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][CH:2]=[CH:14][CH:13]=3)[C:5](=[O:16])[C:6]=2[CH:7]=1

参加物

8

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 136385905HCID 136385905、化合物

生成物 1

HCID 2454892-Methoxyfluoren-9-one収率 71%

試薬・触媒・溶媒 4

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

A solution of 2-hydroxyfluorenone (5 g, 25 5 mmol) in 500 mL methylene chloride was charged with 100 mL solution of 1N NaOH (4 g, 100 mmol), a solution of p-methyl tosylate (9.5 g, 51 mmol) in 200 mL of water and tetrabutylammonium hydrogen sulfate (0.2 g, catalytic) at room temperature. The reaction was monitored by TLC (silica, 25% ethyl acetate in hexane). The reaction mixture was stirred overnight at room temperature, the layers were separated. The organic layer was dried over MgSO. and evaporated. Short path chromatography of the residual solid (silica, 5% ethyl acetate in hexane) afforded 3.8 g (71.0%) of the methylated product.

後処理

  1. customat room temperature
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO
  4. customand evaporated

出典と根拠

ORDレコード
ord-0cc7dcd0f5f741d08ff84b26fe9c9715
出典データセット
uspto-grants-1992_01
特許番号
US05079260

反応ノート

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