5-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid → 5-Methyl-tetrahydro-pyran-2-carboxylic acid

HRID 73204Notes

Reaction equation

HRID 73204 reaction equation
[CH3:1][C:2]1[CH2:7][O:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH:3]=1>CO.[Pt]>[CH3:1][CH:2]1[CH2:7][O:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 553027505-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Product 1

HCID 553027515-Methyl-tetrahydro-pyran-2-carboxylic acidYield 91.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid (40 mg, 0.28 mmol) in MeOH (2.0 mL) was added 5% Pt—C (20 mg), hydrogenated for 16 h at 20 psi. The reaction mixture was filtered off through celite, washed with MeOH and concentration of the filtrate gave 2:1 ratio of geometrical isomers of 5-methyl-tetrahydro-pyran-2-carboxylic acid (37 mg, 91%).

Workup

  1. filtrationThe reaction mixture was filtered off through celite
  2. washwashed with MeOH and concentration of the filtrate

Sources & evidence

ORD record
ord-df350c76740b47538bd5f410f4664009
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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