HCID 69519877, compound → HCID 69517537, compound

HRID 854931Notes

Reaction equation

HRID 854931 reaction equation
[C:1]1([C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]([C:19]([F:22])([F:21])[F:20])[O:16]3)=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[Pd]>[C:1]1([CH:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]([C:19]([F:21])([F:22])[F:20])[O:16]3)=[CH:11][CH:10]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 69519877HCID 69519877, compound

Product 1

HCID 69517537HCID 69517537, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-(1-phenylvinyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 50a, step 4 (2.13 g, 5.69 mmole) and 10% Pd/C (150 mg) in absolute EtOH (30 mL) was hydrogenated at 30 psi for 3 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. Purification of the crude product by silica chromatography (92.5 hexanes:EtOAc) gave 1.62 g (75% yield) of the product as a colorless oil: EIHRMS m/z 376.1279 (M+, C21H19F3O3, Calc'd 376.1286).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the crude product by silica chromatography (92.5 hexanes:EtOAc)

Sources & evidence

ORD record
ord-eda53edaf3384ea3a2a614a4e7e0e98a
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…