Ethyl Acetate → 2-Methoxyfluoren-9-one

HRID 1089829노트

반응식

HRID 1089829 반응식
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

참가 물질

8

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 136385905HCID 136385905, 화합물

생성물 1

HCID 2454892-Methoxyfluoren-9-one수율 71%

시약·촉매·용매 4

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0cc7dcd0f5f741d08ff84b26fe9c9715
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05079260

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