Water → (4-(2,2-Dimethoxyethyl)phenyl)methanol

HRID 2205696노트

반응식

HRID 2205696 반응식
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86720817Methyl 4-(2,2-dimethoxyethyl)benzoate

생성물 1

HCID 84773974(4-(2,2-Dimethoxyethyl)phenyl)methanol수율 62%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 24083Sulfuric acid magnesium salt (1:1)용매

실험 절차

To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%).

후처리

  1. additionadded
  2. filtrationfiltered through celite
  3. washThe filter cake was washed with further ethyl acetate
  4. customThe solvent was evaporated at reduced pressure
  5. customthe residue was purified by flash column chromatography
  6. washeluting with 0-30% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-9c883fa22e8c4143b2260b17dd02849d
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371318B2

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