Ethanol → HCID 84681537, compound

HRID 1477619Notes

Reaction equation

HRID 1477619 reaction equation
C(O)C.[F:4][C:5]([F:18])([F:17])[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][C:9]=2[CH:10]=1.[BH4-].[Na+]>C(O)(=O)C>[F:18][C:5]([F:4])([F:17])[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 84015811HCID 84015811, compound

Product 1

HCID 84681537HCID 84681537, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an ethanol solution (2.0 mL) of 2-(trifluoromethyl)benzofuran-5-carbaldehyde (220 mg, 1.03 mmol) synthesized in Reference Synthesis Example 95, sodium borohydride (115 mg, 3.05 mmol) was added and the resultant solution was stirred at 70° C. for 1 hour and 30 minutes. After completion of the reaction, the reaction solution was cooled to room temperature and acetic acid was added to the cooled solution, followed by concentrating the resultant mixture under reduced pressure. To the obtained residue, water was added and extraction with dichloromethane from the resultant mixture was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (219 mg, yield 99%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationby concentrating the resultant mixture under reduced pressure
  4. additionTo the obtained residue, water was added
  5. extractionextraction with dichloromethane from the resultant mixture
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08bc947a43ca404d8db44e14264a67dc
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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