p-Aminoacetophenone → 4-Amino-alpha-methylbenzenemethanol

HRID 1855130

反応式

HRID 1855130 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ru+2].[Fe]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 7468p-AminoacetophenoneHCID 10340Sodium Carbonate

生成物 1

HCID 857534-Amino-alpha-methylbenzenemethanol

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

Tris(triphenylphosphine)ruthenium(II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Fe, R=t-Bu, Ar=3,5-(CF3)2C6H3—, 1.3 μmol, 0.33 mol %) were dissolved in tetrahydrofuran (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 65° C. After the mixture was cooled to room temperature, p-amino-acetophenone (0.4 mmol), tetrahydrofuran (2 mL) and an aqueous solution of sodium carbonate (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 48 h under H2 (20 atm) at 0° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/1). Accordingly, pure 1-(p-aminophenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

後処理

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 48 h under H2 (20 atm) at 0° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/1)

出典と根拠

ORDレコード
ord-6157bc2378d142439e9752a7b2b93e7f
出典データセット
uspto-grants-2015_02
特許番号
US08962852B2

関連ノート

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