Water → HCID 19994679, compound

HRID 1773227Notes

Reaction equation

HRID 1773227 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH2:12])=O)=[CH:7][C:6]=2[CH:13]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.O>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]#[N:12])=[CH:7][C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 53968927HCID 53968927, compound

Product 1

HCID 19994679HCID 19994679, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the suspension of 5-methylbenzofuran-2-carboxamide (5.17 g, 29.5 mmol) in 66 mL of anhydrous THF was added TEA (8.23 mL, 59.0 mmol). TFAA (6.25 mL, 44.3 mmol) was added dropwise to the above mixture at 0° C. (internal temperature did not exceed 15° C.). After stirring at 0° C. for 1 hr, the reaction was complete by TLC. The reaction mixture was poured into 610 mL of H2O, and extracted with EtOAc 3 times. The organic layer was washed with sat. NaHCO3, brine and dried over Na2SO4, filtered and concentrated under reduced pressure, and the resulting residue was purified by silica gel flash chromatography, 100% Heptane-8% Ethyl Acetate/92% Heptane, to yield 5-methylbenzofuran-2-carbonitrile (3.65 g). 1H NMR (400 MHz, DMSO-d6) δ 2.42 (s, 3H), 7.42 (dd, J=8.6, 1.8 Hz, 1H), 7.59-7.67 (m, 2H), 8.03 (d, J=0.9 Hz, 1H).

Workup

  1. customdid not exceed 15° C.
  2. extractionextracted with EtOAc 3 times
  3. washThe organic layer was washed with sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel flash chromatography, 100% Heptane-8% Ethyl Acetate/92% Heptane

Sources & evidence

ORD record
ord-f5e506d3cfa14605833cb2dec2cd6b48
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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