Formic Acid → HCID 21459434, compound

HRID 1941045Notes

Reaction equation

HRID 1941045 reaction equation
[O:1]1CCCO[CH:2]1[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([F:28])[CH:18]=2)[CH2:11][CH2:10]1.C(O)C.C(O)=O>[Pd].C1(C)C=CC=CC=1>[F:28][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][CH:12]2[CH2:13][CH2:14][CH:9]([CH2:8][CH2:7][CH:2]=[O:1])[CH2:10][CH2:11]2)[CH:22]=[CH:21][C:20]=1[O:23][C:24]([F:26])([F:27])[F:25]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 702EthanolHCID 86751781HCID 86751781, compound

Product 1

HCID 21459434HCID 21459434, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

The above 1-(2-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)vinyl-3-fluoro-4-trifluoromethoxybenzene (5.5 g, 13.7 mmol) was hydrogenated in the presence of 5% Pd/C catalyst (0.3 g) in an ethanol solution, followed by filtering off the catalyst, distilling off the solvent under reduced pressure, adding formic acid (2.8 g, 60.8 mmol) and toluene (50 ml) to the residue, refluxing the mixture for 5 hours, washing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water, drying over MgSO4, and distilling off the solvent, to obtain 3-(4-(2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl)cyclohexyl)propanal (1.76 g, 5.1 mmol). The yield of this product from 1-(2-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)vinyl-3-fluoro-4-trifluoromethoxybenzene was 37.2%.

Workup

  1. filtrationby filtering off the catalyst
  2. distillationdistilling off the solvent under reduced pressure
  3. temperaturerefluxing the mixture for 5 hours
  4. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over MgSO4
  6. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-443ee2c66b2a4a09bb2bb256d9565df9
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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