Ethylene Glycol → 2-(2-(Benzyloxy)ethyl)-2-methyl-1,3-dioxolane

HRID 1645637ノート

反応式

HRID 1645637 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14](O)[CH2:15][OH:16].C(OCC)(OCC)OCC>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH3:12])[O:16][CH2:15][CH2:14][O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 2345114-(Benzyloxy)butan-2-one

生成物 1

HCID 597924662-(2-(Benzyloxy)ethyl)-2-methyl-1,3-dioxolane収率 80.8%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 4-benzyloxy-2-butanone (10 g, 56.1 mmol), ethylene glycol (40 ml, 718 mmol), triethyl orthoformate (9.3 ml, 55.9 mmol) and p-toluenesulfonic acid monohydrate (290 mg, 1.52 mmol) was stirred at room temperature for 13.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (40 ml) was added and the mixture was extracted three times with chloroform (50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient). Desired fractions were concentrated to obtain the title compound (10.08 g, 80.8% yield) as a colorless oil.

後処理

  1. extractionthe mixture was extracted three times with chloroform (50 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient)
  5. concentrationDesired fractions were concentrated

出典と根拠

ORDレコード
ord-547e069fc65a4671b006b58491a3d950
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

反応ノート

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