Methanol → 1-(4-chlorophenyl)-1,3-Propanediol

HRID 341792

반응식

HRID 341792 반응식
C([O:3][C:4](=O)[CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.[H-].C([Al+]C(C)C)(C)C.CO.O>C(Cl)Cl>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([OH:14])[CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 21896610Diisopropylaluminium hydride

생성물 1

HCID 103300821-(4-chlorophenyl)-1,3-Propanediol수율 59.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5.0 g of ethyl-4-chlorobenzoylacetate in 100 ml of methylene chloride cooled to -30° C., 77.3 ml of diisopropylaluminium hydride (1.0 mol/l toluene solution) was added, and the resulting mixture was stirred for 30 minutes and then brought back to room temperature over 3 hours, and 4.14 g of methanol and 24.3 g of water were added carefully, and the mixture was stirred for another 1.5 hours. The precipitate was filtered off, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1), to obtain 2.45 g of the title compound as a pale yellow oily substance.

후처리

  1. waitbrought back to room temperature over 3 hours
  2. stirringthe mixture was stirred for another 1.5 hours
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-bbbe2d4035484addbe187122e4fa8725
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856327

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