Diisobutylaluminum hydride → HCID 58536689, compound

HRID 1406285Notes

Reaction equation

HRID 1406285 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:10](OC)=[O:11])=[N:6][C:7]=1[O:8][CH3:9].CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][OH:11])=[N:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 46311222Methyl 5-bromo-6-methoxypicolinate

Product 1

HCID 58536689HCID 58536689, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5-bromo-6-methoxypicolinate (249 mg, 1.01 mmol) in dichloromethane (10 mL) added DIBAL-H in CH2Cl2 (1M, 3.04 mL) at −78° C. The reaction was immediately warmed to room temperature then stirred at room temperature for 1 hr. LCMS indicated that the reaction was complete. To the reaction mixture was added saturated aqueous NaK tartrate. It was stirred for 30 min. The reaction mixture was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a white solid (205 mg, 93.3%).

Workup

  1. stirringIt was stirred for 30 min
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8253db017f9e4f4ab22df83d54d88246
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

Loading…