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

HRID 1637375

반응식

HRID 1637375 반응식
[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

참가 물질

6

반응물 2

HCID 15349Ethyl benzoylformateHCID 178478989HCID 178478989, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ec4170fa2e8484bba344be707fc2d55
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06040449

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