Methyl morpholine oxide → 1-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol

HRID 1506948ノート

反応式

HRID 1506948 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/C=C/COCOC.C[N+]1([O-])CC[O:19][CH2:18]C1.[CH3:23][C:24]([CH3:26])=[O:25].C[C:28]([OH:31])(C)C.[OH2:32]>O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:23]([OH:32])[CH:24]([OH:25])[CH2:26][O:19][CH2:18][O:31][CH3:28]

参加物

5

反応物 3

HCID 82029Methyl morpholine oxideHCID 86602953Acetone tBuOH WaterHCID 90025785HCID 90025785、化合物

生成物 1

HCID 900190611-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol収率 70%

試薬・触媒・溶媒 1

HCID 30318Osmium Tetroxide触媒

実験手順

(E)-1-chloro-2-(3-(methoxymethoxy)prop-1-enyl)benzene (9.1 g, Preparation Example 2) was dissolved in 45 mL of a mixture of acetone/t-BuOH/H2O (5:1:1 V/V). At room temperature, N-methylmorpholine-N-oxide (7.51 g) and OsO4 (0.54 g) were added thereto and stirred for 2-3 hours. When the reaction was completed, the obtained product was washed with water and methylenechloride (MC). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4), filtrated, and concentrated under reduced pressure. The crude compound was purified by a silica gel column to produce the title compound (7.42 g, 70˜90%).

後処理

  1. washthe obtained product was washed with water and methylenechloride (MC)
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by a silica gel column

出典と根拠

ORDレコード
ord-23dd4a4bbfa7417ab11a7a2c0acff0b8
出典データセット
uspto-grants-2015_12
特許番号
US09221783B2

反応ノート

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