Propionitrile → HCID 57749143, compound

HRID 1874383Notes

Reaction equation

[C:1](#[N:4])[CH2:2][CH3:3].[N+](=[C:7]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-]>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:2]([C:1]1[O:18][C:13]([C:14]([F:15])([F:16])[F:17])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:4]=1)[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of rhodium acetate (100 mg) and propionitrile (15 mL) was added ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate (4.20 g, 20.0 mmol) over 12 hr, and the mixture was stirred at 80° C. for 5 days. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate=90/10→0/100) to give the title compound (2.03 g, 43%) as a yellow oil.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography (hexane/ethyl acetate=90/10→0/100)

Sources & evidence

ORD record: ord-d18adb28d0284521907fd34d33206e95
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

Loading…