Sodium borohydride → (2,6-Dichloropyridin-3-yl)methanol

HRID 2066897Notes

Reaction equation

HRID 2066897 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[C:6]([Cl:12])[N:5]=1>CO>[Cl:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[C:6]([Cl:12])[N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122593832,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 12259932(2,6-Dichloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (125 mg, 4.49 mmol) was added to 2,6-dichloro-pyridine-3-carbaldehyde (0.62 g, 3.5 mmol) in 20 mL of methanol at 0° C. After 30 minutes, the mixture was quenched with NaHCO3 (20 mL) and water (20 mL) and extracted with EtOAc (2×20 mL). The combined extracts were dried and concentrated under vacuum to afford 72a: LC-MS178.0 (MH+)

Workup

  1. customthe mixture was quenched with NaHCO3 (20 mL) and water (20 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4948468dacd54fb58a4772fbfceffa1e
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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