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

HRID 341792

反応式

HRID 341792 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bbbe2d4035484addbe187122e4fa8725
出典データセット
uspto-grants-1999_01
特許番号
US05856327

関連ノート

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