Trifluoroacetic acid → HCID 18467862, compound

HRID 2229485Notes

Reaction equation

HRID 2229485 reaction equation
[CH3:1][C:2]1([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:6][C:5](=[CH2:7])[CH2:4][O:3]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:6][C:5](=[CH2:7])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86758358HCID 86758358, compound

Product 1

HCID 18467862HCID 18467862, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., to a solution of 2-methyl-4-methylene-2-tetrahydrofuroic acid, tert-butyl ester dissolved in 0.3 mL dichloromethane was added 461 mL of a 1:1 solution of trifluoroacetic acid and dichloromethane. After 20 min, the ice bath was removed and the reaction mixture allowed to stir at room temperature for 5 h. The excess trifluoroacetic acid was removed by a stream of nitrogen, and the residue coevaporated with dichloromethane 3 times. The crude product was chromatographed via silica gel (gradient elution 0-12% MeOH/CH2Cl2) to give 55 mg of the desired acid as a glass (77%). Mass Spectrum: EI m/e 142 (M)+.

Workup

  1. customthe ice bath was removed
  2. customThe excess trifluoroacetic acid was removed by a stream of nitrogen
  3. customThe crude product was chromatographed via silica gel (gradient elution 0-12% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ed32c2789d194450905ca71dc3d12a5e
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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