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

HRID 1497907Notes

Reaction equation

HRID 1497907 reaction equation
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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-101a2fea8df141a18d061d33b3967c5a
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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