Formic Acid → HCID 58489133, compound

HRID 2190896Notes

Reaction equation

HRID 2190896 reaction equation
CCC[CH2:4][CH:5]1[O:10][C:9]([CH3:11])=[C:8]([O-])[C:6]1=O.[CH:13]([OH:15])=[O:14].S(=O)(=O)(O)[OH:17].C1[CH2:25][O:24]CC1>>[CH:13]([O:15][CH2:11][C:9]1[O:10][C:5]([CH2:4][O:17][CH:25]=[O:24])=[CH:6][CH:8]=1)=[O:14]

Participants

5

Reactant 4

HCID 284Formic Acid2×HCID 1118Sulfuric Acid2×HCID 8028TetrahydrofuranHCID 25202471HCID 25202471, compound2×

Product 1

HCID 58489133HCID 58489133, compound

Procedure

This example demonstrates that the conversion of BHMF to BFMF proceeds cleanly using formic acid and catalytic amounts of sulfuric acid. In a 50-mL round bottomed flask, BHMF (0.25 g, 2 mmol), formic acid (0.76 mL, 20 mmol), H2SO4 (6.9 μL, 0.13 mmol) were dissolved in THF (5 mL). The solution was heated at reflux for 15 h. The yellow solution was concentrated under reduced pressure, and the resulting oily residue was extracted with CH2Cl2 (10 mL×3). The organic layer was collected and the solvent was evaporated to yield BFMF as a brown oil. Yield: 0.32 g (87%). The intermediate FMHF, which was not isolated, was detected after 2 h (FIGS. 3 and 4).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 15 h
  3. concentrationThe yellow solution was concentrated under reduced pressure
  4. extractionthe resulting oily residue was extracted with CH2Cl2 (10 mL×3)
  5. customThe organic layer was collected
  6. customthe solvent was evaporated
  7. customto yield BFMF as a brown oil
  8. customThe intermediate FMHF, which was not isolated

Sources & evidence

ORD record
ord-65f34540bf414bad8d37905752d73aac
Source dataset
uspto-grants-2012_12
Patent number
US08324409B2

Reaction notes

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