ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)acrylate → ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)propanoate

HRID 71257Notes

Reaction equation

HRID 71257 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>C(O)C.[Pt](=O)=O>[F:22][C:2]([F:1])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 66685135ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)acrylate

Product 1

HCID 66685195ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)propanoateYield 97.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)acrylate (101 mg, 308 μmol) and platinum (IV) oxide (10.3 mg, 46 μmol) in ethanol (2 mL) was hydrogenated at 1 atmosphere for 4.25 h. The catalyst was removed by filtration through a Whatman Autovial filter and the filtrate was concentrated under vacuum to afford ethyl 3-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)propanoate (99 mg, 97% yield) as a viscous colorless oil. 1H NMR (400 MHz, CDCl3): δ ppm 7.34-7.60 (m, 4H), 4.02 (q, 2H), 3.81 (ddd, 2H), 3.43-3.63 (m, 2H), 2.07-2.23 (m, 2H), 1.97-2.04 (m, 2H), 1.84-1.96 (m, 4H), 1.19 (t, 3H).

Workup

  1. customThe catalyst was removed by filtration through a Whatman Autovial
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8af5b5e2aa464a9dba1c23e8684ff900
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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