Ethanol → HCID 86752838, compound

HRID 964919Notes

Reaction equation

HRID 964919 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH:10]2[CH2:12][CH2:11]2)=O)=[CH:6][N:5]=[C:4]([CH:13]([F:15])[F:14])[N:3]=1.C([OH:18])C>CC(C)=O>[Cl:1][C:2]1[C:7]([CH2:8][C:10]2([OH:18])[CH2:12][CH2:11]2)=[CH:6][N:5]=[C:4]([CH:13]([F:15])[F:14])[N:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 86752839HCID 86752839, compound

Product 1

HCID 86752838HCID 86752838, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

70 g of 4-chlorodifluoromethyl-5-cyclopropylcarbonylpyrimidine was added to 100 ml of ethanol, then, 15 g of a t-butylamine borane complex was further added under cooling with ice, and the mixture was stirred at room temperature for 2 hours. After addition of 30 ml of acetone, the mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. 100 ml of water was added to the residue, and extraction with ethyl acetate was carried out. The extract layer was washed with water, and the solvent was distilled off under reduced pressure. The residue was dried in vacuum to obtain 45 g of the desired product. nD20.5 1.5020

Workup

  1. addition15 g of a t-butylamine borane complex was further added
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. distillationthe solvent was distilled off under reduced pressure
  5. addition100 ml of water was added to the residue, and extraction with ethyl acetate
  6. washThe extract layer was washed with water
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-ffed97e330fa49a18ee0a687893810e6
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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