Diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate → Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

HRID 1497907노트

반응식

HRID 1497907 반응식
C([O:8][CH:9]1[CH2:12][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10]1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH:9]1[CH2:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10]1

참가 물질

4

반응물 1

HCID 12815110Diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate

생성물 1

HCID 14728564Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate (158) (1.43 g, 4.7 mmol) in EtOH (18 mL) was added 10% palladium on carbon (143 mg) and the mixture was hydrogenated with a H2 balloon for 12 hours at room temperature. The catalyst was removed by filtration using celite, washed with ethyl acetate and EtOH and the solvent was removed under reduced pressure. The crude product was purified via column chromatography using hexanes/ethyl acetate as eluent to yield diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (159). 1H NMR (400 MHz, CD2Cl2) δ 4.4-4.32 (m, 1H), 4.21 (qd, J=7.2, 2.0 Hz, 4H), 2.89-2.84 (m, 2H), 2.46-2.41 (m, 2H), 2.20 (d, J=6.4 Hz, 1H), 1.27 (t, J=7.2 Hz, 6H). MS m/z 217.1 (M+1)+.

후처리

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate and EtOH
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified via column chromatography

출처 및 근거

ORD 기록
ord-101a2fea8df141a18d061d33b3967c5a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199981B2

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