Diethyl 1,1-cyclobutanedicarboxylate → Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

HRID 1802424노트

반응식

HRID 1802424 반응식
[Li+].CC(O[Al-](OC(C)(C)C)OC(C)(C)C)(C)C.[C:18]1([C:27](OCC)=[O:28])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19]1.OS([O-])(=O)=O.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:25]([O:24][C:22]([C:18]1([CH2:27][OH:28])[CH2:21][CH2:20][CH2:19]1)=[O:23])[CH3:26]

참가 물질

6

반응물 3

HCID 77410Diethyl 1,1-cyclobutanedicarboxylateHCID 516920Potassium bisulfateHCID 16688073Lithium aluminum-tri-tert-butoxyhydride

생성물 1

HCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate수율 63.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of lithium aluminum-tri-tert-butoxyhydride 1.0M in THF (100.0 mL, 100.0 mmol) is added at −78° C. to a solution of diethyl 1,1-cyclobutanedicarboxylate (10.0 g, 50.0 mmol) in anhydrous THF (50.0 mL). After stirring the reaction mixture at room temperature for 14 h, 10% aq. KHSO4 solution is added and the reaction mixture diluted with ethyl acetate. After separating the two phases, the organic phase is washed with water and brine and dried over anhydrous Na2SO4. Filtration and removal of the solvent under reduced pressure affords 5.0 g of 1-hydroxymethyl-cyclobutanecarboxylic acid ethyl ester that is used in the next step without further purification. Yield: 63%; m/z 159 [M+H].

후처리

  1. customAfter separating the two phases
  2. washthe organic phase is washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationFiltration and removal of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-7a43ee4e4b0e4a099f7ffff246c0a9e8
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349871B2

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