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

HRID 31689

反応式

HRID 31689 の反応式
[CH2:1]([O:8][CH2:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].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][C:10]1([CH3:11])[O:15][CH2:14][CH2:13][O:12]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 36912841-(Benzyloxy)propan-2-one

生成物 1

HCID 597925942-((Benzyloxy)methyl)-2-methyl-1,3-dioxolane収率 90.5%

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 1-benzyloxy-2-propanone (4.94 g, 30.1 mmol), ethylene glycol (20 ml, 359 mmol), triethyl orthoformate (5 ml, 30.1 mmol), and p-toluenesulfonic acid monohydrate (130 mg, 0.683 mmol) was stirred at room temperature for 61.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (20 ml) was added and the mixture was extracted twice with chloroform (50 ml) and 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 (5.67 g, 90.5% yield) as a colorless oil.

後処理

  1. extractionthe mixture was extracted twice 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-4e1336d1e5884c6ca1ba3b640ca449a4
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

関連ノート

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