Diisobutylaluminumhydride → (5-Nitropyridin-2-yl)methanol

HRID 2409714Notes

Reaction equation

HRID 2409714 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=O)C>C(Cl)Cl>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:14][OH:13])=[N:17][CH:18]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 45116302Ethyl 5-nitropicolinate

Product 1

HCID 20583228(5-Nitropyridin-2-yl)methanolYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminium hydride (1 M in DCM, 41.6 mL, 41.6 mmol, 1.3 equiv) was added dropwise to a cold (−78° C.) solution of 5-nitro-pyridine-2-carboxylic acid ethyl ester (Step 39.4) (6.4 g, 32 mmol) in DCM (120 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt, quenched by addition of an aqueous solution of potassium sodium tartrate, diluted with DCM and H2O, and filtered through a pad of celite. The filtrate was extracted several times with DCM. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1) to provide 1.44 g of the title compound: ESI-MS: 153.1 [M−H]−.

Workup

  1. customquenched by addition of an aqueous solution of potassium sodium tartrate
  2. additiondiluted with DCM and H2O
  3. filtrationfiltered through a pad of celite
  4. extractionThe filtrate was extracted several times with DCM
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1)

Sources & evidence

ORD record
ord-cad2139589e64dff8b0e1fc9d8749a4d
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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