Dimethylformamide → HCID 90423657, compound

HRID 2272522Notes

Reaction equation

HRID 2272522 reaction equation
I[CH:2]([CH3:4])[CH3:3].[CH:5]1([C:8]2[C:15]([CH:16]3[CH2:18][CH2:17]3)=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([OH:19])[C:9]=2[F:20])[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:5]1([C:8]2[C:15]([CH:16]3[CH2:18][CH2:17]3)=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([O:19][CH:2]([CH3:4])[CH3:3])[C:9]=2[F:20])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 904235374,5-Dicyclopropyl-3-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 90423657HCID 90423657, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Iodopropane (862 mg) was added at room temperature to a mixture of 4,5-dicyclopropyl-3-fluoro-2-hydroxybenzaldehyde (744 mg), potassium carbonate (934 mg), and DMF (20 mL), and the mixture was stirred at 60 C for 2 hours in a nitrogen atmosphere. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (865 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-597734d31b944e28b5bd77530c42b910
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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