Tetrahydrofuran → HCID 22220046, compound

HRID 606814Notes

Reaction equation

HRID 606814 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5].O1CCCC1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 22220046HCID 22220046, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 2-fluoro-5-iodobenzaldehyde, (prepared essentially as described in Tet. Lett., 33, 7499, (1992)), (6.54 g, 26.1 mmol) in 4:1 tetrahydrofuran:methanol (200 mL) and treat with sodium borohydride (1.98 g, 52.3 mmol) and stir overnight. Concentrate the reaction mixture, then partition between ethyl acetate and water. Wash the organic layer with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter, and concentrate. Purify the crude oil by silica gel chromatography, eluting with 85:15 hexanes:ethyl acetate, to give the title compound as a white crystalline solid (5.8 g, 88%).

Workup

  1. custom(prepared essentially
  2. concentrationConcentrate the reaction mixture
  3. custompartition between ethyl acetate and water
  4. washWash the organic layer with an aqueous saturated solution of sodium chloride
  5. dry with materialdry (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude oil by silica gel chromatography
  9. washeluting with 85:15 hexanes

Sources & evidence

ORD record
ord-24ed926d20494ef9b8b8d2f966fa1a67
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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