3-ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-2H-chromene → 3-Ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-chroman

HRID 1032436Notes

Reaction equation

HRID 1032436 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8]([CH3:19])([CH3:18])[O:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([F:17])=[CH:12][CH:11]=2)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:17])[CH:14]=2)[O:9][C:8]1([CH3:18])[CH3:19])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 540126573-ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-2H-chromene

Product 1

HCID 543008663-Ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-chromanYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

140 mg of palladium-on-carbon (5%) are added to a solution of 3.4 g (13 mmol) of 3-ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-2H-chromene in 30 ml of absolute ethanol and the mixture is hydrogenated at normal pressure and room temperature for 90 minutes. The catalyst is then filtered off and the filtrate is concentrated by evaporation in vacuo, yielding 3.47 g of 3-ethoxycarbonylmethyl-2,2-dimethyl-6-fluoro-chroman in the form of a light-yellow oil.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-7275bce4e428419f91eccc8d7a6c1dbb
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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