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

HRID 31692노트

반응식

HRID 31692 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4bc513ce0dfc42259687f0217e5bcc1d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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