Ethanol → HCID 89656502, compound

HRID 930918Notes

Reaction equation

HRID 930918 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])[CH:5]=[O:6].C(O)C.[BH4-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86704958HCID 86704958, compound

Product 1

HCID 89656502HCID 89656502, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 287a (3.76 g, 12 mmol) in the mixture of ethanol (10 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (0.136 g, 3.60 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. The solvent was evaporated and the residue was partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (3.72 g, 98%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned with ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5a48091fc6b4c18bd4f56f5b7ba3223
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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