Water → HCID 23130566, compound

HRID 2080083Notes

Reaction equation

HRID 2080083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[O:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1.[BH4-].[Na+].O.C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[O:10][C:9]([CH2:11][OH:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 23130457HCID 23130457, compound

Product 1

HCID 23130566HCID 23130566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-fluoro-phenoxy)-furan-2-carbaldehyde described in Preparation Example 50 (1.5 g, 7.3 mmol) in tetrahydrofuran (20 mL) was added sodium borohydride (280 mg, 7.3 mmol), and the solution was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice, and the organic layer was filtered through a glass filter lined with silica gel. The solvent was evaporated in vacuo, and the title compound (1.5 g, 7.2 mmol) was obtained as a pale yellow oil.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. filtrationthe organic layer was filtered through a glass
  4. filtrationfilter
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-845789c2c4414216afbd31ab59075f56
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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