Methyl iodide → methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

HRID 2399775

반응식

HRID 2399775 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](=O)([O:15]C)[O:13][CH3:14].[H-].[Na+].[CH3:20]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([CH3:20])([C:12]([O:13][CH3:14])=[O:15])[CH2:5]2

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanone

생성물 1

HCID 19384693methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-chloroindanone (10 g) and dimethyl carbonate (6.0 ml) in THF (80 ml) was added a 60% oil dispersion (5.0 g) of sodium hydride at room temperature, followed by heating at reflux for 12 hours. After cooling to room temperature, methyl iodide (5.0 ml) was added thereto, and the mixture was heated again at reflux for 12 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane (300 ml×3). The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate (yield, 5.3 g).

후처리

  1. temperatureby heating
  2. temperatureat reflux for 12 hours
  3. temperaturethe mixture was heated again
  4. temperatureat reflux for 12 hours
  5. extractionextracted with dichloromethane (300 ml×3)
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4e6f8a3052034b5c93c5d14b1b1f8695
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05451607

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