ethyl 8-but-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate → ethyl 8-butyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854917Notes

Reaction equation

HRID 854917 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([O:24][C:25]([F:28])([F:27])[F:26])[CH:8]=[C:9]2[C:14]=1[O:13][CH:12]([C:15]([F:18])([F:17])[F:16])[C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10]2)#[C:2][CH2:3][CH3:4]>C(O)C.[Pd]>[CH2:1]([C:5]1[CH:6]=[C:7]([O:24][C:25]([F:28])([F:26])[F:27])[CH:8]=[C:9]2[C:14]=1[O:13][CH:12]([C:15]([F:16])([F:17])[F:18])[C:11]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 86599466ethyl 8-but-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 86599467ethyl 8-butyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 8-but-1-ynyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21q, Step 1 (450 mg, 1.10 mmole) and 10% Pd/C (45 mg) in absolute ethanol was hydrogenated at 30 psi for 1.5 h. The catalyst was removed by filtration and the solvent was removed in vacuo to give 310 mg (68% yield) of the product as a yellow crystalline solid: EIHRMS m/z 412.1099 (M+, C18H18F6O4, Calc'd 412.1109).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6f46383d7bf74db9bc60024856a53b32
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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