HCID 86690121, compound → 1447943-09-0

HRID 520416Notes

Reaction equation

HRID 520416 reaction equation
C([O:8][CH2:9][C:10]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][CH2:12][O:11]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C:10]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][CH2:12][O:11]1

Participants

4

Reactant 1

HCID 86690121HCID 86690121, compound

Product 1

HCID 866901201447943-09-0Yield 178.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (80 mg, 0.753 mmol) was added under nitrogen to a solution of methyl 2-((benzyloxy)methyl)tetrahydrofuran-2-carboxylate (377 mg, 1.506 mmol) in MeOH (20 mL) in a Parr shaker bottle and hydrogenated at 30 psi overnight. The suspension was filtered and the filtrate was evaporated to dryness to afford methyl 2-(hydroxymethyl)tetrahydrofuran-2-carboxylate as a clear oil (0.43 g, 97.5%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 4.10-3.98 (m, 2H), 3.85 (d, J=11.4 Hz, 1H), 3.78 (s, 3H), 3.69 (d, J=11.4 Hz, 1H), 2.19-2.12 (m, 1H), 2.09-2.02 (m, 1H), 2.01-1.93 (m, 2H).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-dcac1a5f3a5a49f69855bab980695c17
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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