Water → Ethyl 2-(5,5,6,6,6-pentafluorohexyl)-9-decenoate

HRID 1267747Notes

Reaction equation

[Cl-].[Li+].O.[CH2:4]([C:12]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])(C(OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]>CS(C)=O>[F:32][C:27]([F:33])([C:28]([F:29])([F:30])[F:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH:12]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 180 °C

Procedure

Lithium chloride (401 mg, 9.540 mmol) and water (86 mg, 4.770 mmol) were added to a solution of diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonate (2.12 g, 4.770 mmol) in dimethyl sulfoxide (8 ml) followed by stirring for 16 hours at 180° C. After cooling, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/50) to give ethyl 2-(5,5,6,6,6-pentafluorohexyl)-9-decenoate (1.40 g, Yield 79%) as a colorless oil.

Workup

temperatureAfter cooling
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/50)

Sources & evidence

ORD record: ord-d9462a806804465990ad6b22700b72da
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552068B1

Reaction notes

Loading…