Sodium Carbonate → 1-(3,4-Dimethoxyphenyl)ethanol

HRID 1855134ノート

反応式

HRID 1855134 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ru+2].[Fe]>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

参加物

6

反応物 2

HCID 10340Sodium CarbonateHCID 143283,4-Dimethoxyphenyl methyl ketone

生成物 1

HCID 4364381-(3,4-Dimethoxyphenyl)ethanol

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride触媒HCID 1140Toluene溶媒2 回

反応条件

温度
120 °C

実験手順

Tris(triphenylphosphine)ruthenium(II) chloride (0.38 mg, 0.4 μmol, 0.1 mol %) and a chiral ligand (M=Fe, R=t-Bu, Ar=C6H5—, 0.26 μmol, 0.065 mol %) were dissolved in toluene (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 120° C. After the mixture was cooled to room temperature, 3,4-dimethoxyacetophenone (0.4 mmol), toluene (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 24 h under H2 (10 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(3,4-dimethoxyphenyl)ethanol was obtained and the ee value (ee=96%) was measured by GC analysis.

後処理

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (10 atm) at 25° 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=1/5)

出典と根拠

ORDレコード
ord-7e3c47d2d0d34f0fa0339c1be3948d90
出典データセット
uspto-grants-2015_02
特許番号
US08962852B2

反応ノート

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