Ethyl ketone → 4-((Benzyloxy)methyl)-2,2-diethyl-1,3-dioxolane

HRID 31685

반응식

HRID 31685 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])=[CH:3][CH:2]=1.[CH3:14][CH2:15][C:16](=O)[CH2:17][CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:7]([O:8][CH2:9][CH:10]1[CH2:11][O:12][C:16]([CH2:17][CH3:18])([CH2:15][CH3:14])[O:13]1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 7288Ethyl ketoneHCID 980723-(Benzyloxy)-1,2-propanediolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 597925274-((Benzyloxy)methyl)-2,2-diethyl-1,3-dioxolane수율 67.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a tetrahydrofuran (30 ml) solution of DL-α-O-benzyl glycerol (3 g, 16.5 mmol), 3-pentanone (17.5 ml, 165 mmol) and p-toluenesulfonic acid monohydrate (300 mg, 1.58 mmol) were added at room temperature and the mixture was stirred at the same temperature for 22 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (5 ml) was added to adjust pH to about 8. The generated precipitate was removed by filtration and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 3/1 gradient). A desired fraction was concentrated to obtain the title compound (2.77 g, 67.1% yield) as a colorless oil.

후처리

  1. customThe generated precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 3/1 gradient)
  4. concentrationA desired fraction was concentrated

출처 및 근거

ORD 기록
ord-b0ba235f52084fb9baa50225f74f6979
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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