Ethyl 1-benzyloxymethylcyclobutanecarboxylate → Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

HRID 231605Notes

Reaction equation

HRID 231605 reaction equation
C([O:8][CH2:9][C:10]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][CH2:11]1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][CH2:9][C:10]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 15632047Ethyl 1-benzyloxymethylcyclobutanecarboxylate

Product 1

HCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 1-benzyloxymethylcyclobutanecarboxylate (6.57 g, 26.5 mmol), 10% palladium on carbon (0.4 g) and ethanol (100 ml) was hydrogenated on a Parr Shaker for 4 hours. The catalyst was removed by filtration. The filtrate was evaporated in vacuo to leave the desired product as a colorless oil: NMR (CDCl3) δ32 1.26 (3H, t, J=7 Hz), 1.8~2.6 (6H, m), 2.61 (H, s), 3.78 (2H, s), 4.15 (2H, q, J=7 Hz).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-219137ec4d1340f2b1324db4babbf88f
Source dataset
uspto-grants-1989_07
Patent number
US04847306

Reaction notes

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