Dimethyl Carbonate → 1H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester

HRID 1503

반응식

HRID 1503 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7]2.[H][H].[CH3:16][O:17][C:18](=O)[O:19]C>C(COC)OC>[C:18]([CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([Cl:3])[CH:5]=2)[C:9]1=[O:13])([O:17][CH3:16])=[O:19]

참가 물질

6

반응물 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 110423911H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester수율 45%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
60 °C

실험 절차

To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid.

후처리

  1. additionwas added dropwise at room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 100 ml H2O
  4. extractionextracted with ethyl ether (3×100 ml)
  5. extractionThe ether extract
  6. washwas washed with brine (100 ml)
  7. dry with materialdried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-54e336ac6c4f4117baf301a34b00c11e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726162

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