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

HRID 1497907ノート

反応式

HRID 1497907 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-101a2fea8df141a18d061d33b3967c5a
出典データセット
uspto-grants-2015_12
特許番号
US09199981B2

反応ノート

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