Sodium borohydride → (6-Iodopyridin-3-yl)methanol

HRID 1864571Notes

Reaction equation

HRID 1864571 reaction equation
[I:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[BH4-].[Na+]>C(O)C>[I:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10891136Ethyl6-iodonicotinoate

Product 1

HCID 23039516(6-Iodopyridin-3-yl)methanolYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

30 g (108 mmol) of ethyl 6-iodonicotinate dissolved in 300 ml of ethanol are added dropwise to a solution of 20.5 g (542 mmol) of sodium borohydride in 200 ml of ethanol, cooled beforehand to 0° C. The reaction medium is allowed to warm to room temperature and is then stirred for 1 hour 30 minutes at room temperature. The reaction medium is hydrolysed and extracted with ethyl acetate. The boron salts precipitate out, and the medium is filtered and then evaporated to dryness. The reaction medium is taken up in dichloromethane, the product precipitates out, isopropyl ether is added and the medium is filtered. The precipitate is washed with isopropyl ether. 17 g (67%) of (6-iodopyrid-3-yl)methanol are obtained in the form of a pale yellow solid with a melting point of 102° C.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe boron salts precipitate out
  4. filtrationthe medium is filtered
  5. customevaporated to dryness
  6. customthe product precipitates out
  7. additionisopropyl ether is added
  8. filtrationthe medium is filtered
  9. washThe precipitate is washed with isopropyl ether

Sources & evidence

ORD record
ord-de2e2c6d229048b58e8e118aba2a180b
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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