HCID 86690124, compound → HCID 86690125, compound

HRID 520419Notes

Reaction equation

HRID 520419 reaction equation
[F:1][C:2]1([F:14])[CH:7]=[CH:6][CH2:5][O:4][C:3]1([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>CCOC(C)=O.[Pd]>[F:14][C:2]1([F:1])[CH2:7][CH2:6][CH2:5][O:4][C:3]1([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 86690124HCID 86690124, compound

Product 1

HCID 86690125HCID 86690125, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 10% Pd—C (37.5 mg, 0.035 mmol) in a solution of ethyl 3,3-difluoro-2-methyl-3,6-dihydro-2H-pyran-2-carboxylate in EtOAc (10 mL) was hydrogenated under balloon pressure for 1 h. The suspension filtered and evaporated to dryness to yield ethyl 3,3-difluoro-2-methyltetrahydro-2H-pyran-2-carboxylate as a clear oil (136 mg, 96%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.35-4.24 (m, 2H), 3.89-3.80 (m, 1H), 3.78-3.69 (m, 1H), 2.34-2.09 (m, 2H), 2.03-1.90 (m, 1H), 1.85-1.75 (m, 1H), 1.57-1.51 (m, J=1.5, 0.5 Hz, 3H), 1.34 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe suspension filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-8cbc049e761244c59726fbc5df66e589
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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