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

HRID 1506948노트

반응식

HRID 1506948 반응식
[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]

참가 물질

5

반응물 3

HCID 82029Methyl morpholine oxideHCID 86602953Acetone tBuOH WaterHCID 90025785HCID 90025785, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-23dd4a4bbfa7417ab11a7a2c0acff0b8
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221783B2

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