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

HRID 877318ノート

反応式

HRID 877318 の反応式
[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

参加物

8

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86720817Methyl 4-(2,2-dimethoxyethyl)benzoate

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 24083Sulfuric acid magnesium salt (1:1)溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4b435769edb041189235737fdf98ae33
出典データセット
uspto-grants-2015_03
特許番号
US08987299B2

反応ノート

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