Ethanol → HCID 87426228, compound

HRID 623505Notes

Reaction equation

HRID 623505 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:8]([C:9](OCC)=[O:10])=[CH:7][N:6]=1.[BH4-].[Na+].[Cl-].[Li+].C(O)C>C1COCC1>[F:21][C:2]([F:1])([F:20])[CH2:3][O:4][C:5]1[N:6]=[CH:7][C:8]([CH2:9][OH:10])=[CH:14][C:15]=1[C:16]([F:19])([F:17])[F:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 87426687HCID 87426687, compound

Product 1

HCID 87426228HCID 87426228, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 6-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)nicotinate (250 mg, 0.79 mmol), sodium borohydride (158 mg, 3.94 mmol), and lithium chloride (167 mg, 3.94 mmol) in THF (3 mL) is added ethanol (3 mL), and the mixture is stirred at room temperature for 4 hours. After cooling to 0° C., the reaction is quenched with water (100 mL) and extracted with EtOAc (100 mL). The separated organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1) to give 62 mg (29% yield) of the title compound as green oil.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction is quenched with water (100 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. dry with materialThe separated organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1)

Sources & evidence

ORD record
ord-cc68a7a0ce0b4f2982e9a417d42a905e
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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