Lithium borohydride → HCID 19996530, compound

HRID 1607596Notes

Reaction equation

HRID 1607596 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[C:10](=[O:26])[CH:9]=1)=O)C>O1CCCC1>[OH:5][CH2:6][C:8]1[CH:13]=[CH:12][N:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:22])[F:23])=[CH:16][C:15]=2[Cl:25])[C:10](=[O:26])[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 19996513HCID 19996513, compound2×

Product 1

HCID 19996530HCID 19996530, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium borohydride (0.32 g, 14.5 mmol) suspended in tetrahydrofuran (10 ml) was added a solution of 4-ethoxy carbonyl-1-2,6 dichloro-4-trifluoromethylphenyl)-2-pyridone (Compound 1, 10 g, 26 mmol) in tetrahydrofuran (30 ml). The mixture was heated under reflux for two hours, allowed to cool to room temperature and the solvent removed in vacuo. The residue was shaken with water and ethyl acetate, the layers separated, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, then brine, dried over magnesium sulphate and evaporated in vacuo to give 4-hydroxymethyl-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-2-pyridone as a brown gum (9.2 g) (Compound 13).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two hours
  3. customthe solvent removed in vacuo
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. dry with materialbrine, dried over magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-57906d47a9ed46acb9a1a4841eed8883
Source dataset
uspto-grants-1989_09
Patent number
US04866078

Reaction notes

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