Ethyl benzoylformate → Ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate

HRID 1637375

反応式

HRID 1637375 の反応式
[C:1]1([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]1([Mg]Cl)[CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1.C(OCC)C.C(OCC)(=O)C>[CH:14]1([C:7]([OH:13])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

6

反応物 2

HCID 15349Ethyl benzoylformateHCID 178478989HCID 178478989、化合物

生成物 1

HCID 12322152Ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 23.5 g of ethyl phenylglyoxylate in 200 ml of tetrahydrofuran, 70 ml of 2.0 M cyclopentylmagnesium chloride solution in diethyl ether was added dropwise under cooling with ice, followed by stirring for 30 minutes at the same temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution and brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=30/1-20/1) to provide 11 g of ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate, which was dissolved in 40 ml of methanol. To the solution 20 ml of 4N aqueous sodium hydroxide solution was added at room temperature, followed by stirring for 2 hours at the same temperature and further for 1 hour at 50° C. Distilling the methanol off under reduced pressure, the aqueous layer was made weakly acidic with 4N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and then brine and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was washed with 1:1 mixture of diethyl ether and hexane. Thus, 8.7 g of the title compound was obtained.

後処理

  1. temperatureunder cooling with ice
  2. washwashed with saturated aqueous ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=30/1-20/1)

出典と根拠

ORDレコード
ord-3ec4170fa2e8484bba344be707fc2d55
出典データセット
uspto-grants-2000_03
特許番号
US06040449

関連ノート

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