HCID 86690114, compound → HCID 86690113, compound

HRID 520403Notes

Reaction equation

HRID 520403 reaction equation
[F:1][C:2]1([F:19])[CH2:7][O:6][C:5]([CH3:18])([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:4][CH2:3]1>CO.[Pd]>[F:19][C:2]1([F:1])[CH2:7][O:6][C:5]([CH3:18])([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 86690114HCID 86690114, compound

Product 1

HCID 86690113HCID 86690113, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of benzyl 5,5-difluoro-2-methyltetrahydro-2H-pyran-2-carboxylate (0.22 g, 0.814 mmol) in MeOH (5 mL) was added 10% Pd/C (0.12 g). The reaction mixture was stirred under H2 for 1 h. The reaction was filtered and concentrated to dryness to yield 5,5-difluoro-2-methyltetrahydro-2H-pyran-2-carboxylic acid (100 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.79-3.91 (2H, m), 2.29-2.42 (1H, m), 2.12-2.26 (1H, m), 1.85-2.08 (2H, m), 1.54 (3H, s).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3c40170d97b5442abb58cff4f2647e2d
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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