Pyridine → HCID 86597332, compound

HRID 2182191Notes

Reaction equation

[F:1][C:2]([F:12])([C:5]([F:11])([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].N1C=CC=CC=1.[Cl-].[C:20]([O:27][CH2:28][CH:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][CH3:33])(=[O:26])/[CH:21]=[CH:22]\[C:23]([O-])=[O:24].C(OCC)(=O)C>C(#N)C>[C:20]([O:27][CH2:28][CH:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][CH3:33])(=[O:26])/[CH:21]=[CH:22]\[C:23]([O:4][CH2:3][C:2]([F:12])([F:1])[C:5]([F:10])([F:11])[C:6]([F:7])([F:8])[F:9])=[O:24]

Participants

Conditions

Temperature: 20 °C

Procedure

2,2,3,3,4,4,4-Heptafluorobutanol (66.8 g, 0.334 mol) and pyridine (29.6 mL, 0.367 mol) were dissolved in acetonitrile (180 mL) and added with mono(2-ethylhexyl) maleate chloride (90.6 g, 0.367 mol), while-the internal temperature was maintained at 20° C. or lower on an ice bath. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour and added with ethyl acetate (1000 mL). The organic phase was washed with 1 mol/L aqueous hydrochloric acid and a saturated sodium chloride aqueous solution. Then, the organic phase was collected, the organic solvent was evaporated under reduced pressure, and residue was purified by silica gel column chromatography (hexane/chloroform=10/0 to 7/3 (v/v)) to obtain the target compound (80.3 g, yield: 59%) as a colorless transparent oily compound.

Workup

additionAfter completion of the addition
washThe organic phase was washed with 1 mol/L aqueous hydrochloric acid
customThen, the organic phase was collected
customthe organic solvent was evaporated under reduced pressure, and residue
customwas purified by silica gel column chromatography (hexane/chloroform=10/0 to 7/3 (v/v))

Sources & evidence

ORD record: ord-96e0a6e5c0584fa896a4daf54d9bb0c9
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897013B2

Reaction notes

Loading…