Sodium borohydride → (2-Fluoro-4-iodopyridin-3-yl)methanol

HRID 47359Notes

Reaction equation

HRID 47359 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([CH:10]=[O:11])=[C:8]([I:12])[CH:7]=[CH:6][N:5]=1>O1CCCC1>[F:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([I:12])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 11021396(2-Fluoro-4-iodopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.72 g (19.2 mmol) of sodium borohydride is added to a solution of 4 g (16 mmol) of 2-fluoro-4-iodo-3-pyridinecarbaldehyde (described in J.O.C., 1993, 58, pp. 7832) in 100 ml of tetrahydrofuran. The mixture is stirred at room temperature for 4 hours and then hydrolysed. The reaction mixture is extracted with ethyl acetate. The organic phases are dried and concentrated to yield the expected product.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. customThe organic phases are dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d094e11700ea421e989ed6c166b22473
Source dataset
uspto-grants-2004_03
Patent number
US06699876B2

Reaction notes

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