Sodium borohydride → HCID 68922230, compound

HRID 706551Notes

Reaction equation

HRID 706551 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 193617216-Cyclopropylpicolinaldehyde

Product 1

HCID 68922230HCID 68922230, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6-cyclopropylpicolinaldehyde (3.5 g, 23.8 mmol) in methanol (95 mL) chilled to 0° C. was added sodium borohydride (2.70 g, 37.8 mmol). Once addition was complete, the cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. The mixture was concentrated under reduced pressure and the resulting residue was taken up in water, extracted with EtOAc, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (100% EtOAc as the eluent) of the crude material afforded 2.20 g (62%) of the title compound.

Workup

  1. additionOnce addition
  2. customthe cooling bath was removed
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionextracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c0f258350bc406ab3c97d592a504bfa
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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