Ethylene Glycol → 2-(2-Ethyl-[1,3]dioxolan-2-yl)fluoroacetic acid methyl ester

HRID 1096807Notes

Reaction equation

HRID 1096807 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]([F:9])[C:5](=[O:8])[CH2:6][CH3:7].[CH2:11](O)[CH2:12][OH:13].B(F)(F)F.CCOCC>C1CCCCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([F:9])[C:5]1([CH2:6][CH3:7])[O:13][CH2:12][CH2:11][O:8]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 10219521Methyl 2-fluoro-3-oxopentanoate

Product 1

HCID 866370542-(2-Ethyl-[1,3]dioxolan-2-yl)fluoroacetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-3-oxopentanoic acid methyl ester (2.21 g, 14.9 mmol), ethylene glycol (4.15 mL, 74.5 mmol), and BF3.Et2O (0.189 mL, 1.49 mmol) were mixed in cyclohexane (10 mL). The mixture was heated to reflux for 5 h, and allowed to cool to rt. The mixture was diluted with EtOAc, and washed with brine, water, aq. sat. NaHCO3, and brine again. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The title compound was obtained as an oil (1.88 g, 52%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h
  3. washwashed with brine, water, aq. sat. NaHCO3, and brine again
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-5ff2c256654249219f368c1248a6f9b0
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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