Diisobutylaluminum hydride → HCID 59278372, compound

HRID 559709Notes

Reaction equation

HRID 559709 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([Br:11])[CH:5]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Br:11][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([CH3:10])[N:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 40425123Methyl 2-bromo-6-methylpyridine-4-carboxylate

Product 1

HCID 59278372HCID 59278372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (−78° C.) solution of 2-bromo-6-methyl-isonicotinic acid methyl ester (1.90 g, 8.26 mmol) in CH2Cl2 (200 mL) was added a 1 M solution of DIBAH (24.8 mL, 24.8 mmol) in CH2Cl2. The mixture was allowed to warm to room temperature. After 12 hours, the reaction was quenched with saturated aqueous sodium bicarbonate (100 mL). After 5 hours, phases were separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in heptane to afford (2-bromo-6-methyl-pyridin-4-yl)-methanol as white solid. MS m/z 202.45 (M+), 204.44 (M+2).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate (100 mL)
  2. waitAfter 5 hours
  3. customphases were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-182afc03df3747768eca984f98195814
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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