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

HRID 2174

反応式

HRID 2174 の反応式
[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]

参加物

6

反応物 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanoneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cf41a524c8b40e093b3d619340e8c02
出典データセット
uspto-grants-1998_03
特許番号
US05728715

関連ノート

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