Diisobutylaluminum hydride → (3,5-Diethoxypyridin-2-yl)methanol

HRID 1609829Notes

Reaction equation

HRID 1609829 reaction equation
C([O:3][C:4]([C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[CH:8][N:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C1COCC1>[CH2:13]([O:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([O:15][CH2:16][CH3:17])[CH:10]=1)[CH3:14]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69650025HCID 69650025, compound

Product 1

HCID 22260398(3,5-Diethoxypyridin-2-yl)methanolYield 80.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the 3,5-diethoxy-pyridine-2-carboxylic acid ethyl ester solution (250 mg, 1.04 mmol) in CH2Cl2 (10 ml), a solution of DIBAL in THF (1N, 3 mL) is added, and stirred at room temperature for 20 minutes. Excess reagent is quenched with Glauber's salt (Na2H2SO4·10H2O), filtered and concentrated to afford (3,5-diethoxy-pyridin-2-yl)-methanol (166 mg, 80% yield); 1H NMR (300 MHz, CDCl3): 7.77 (s, 1H), 6.69 (s, 1H), 4.65 (s, 2H), 4.15 (q, J=6.9 Hz, 2H), 3.65 (q, J=6.9 Hz, 2H), 1.45 (t, J=6.9 Hz, 6H).

Workup

  1. customExcess reagent is quenched with Glauber's salt (Na2H2SO4·10H2O)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eba854ff12154a10b7f305c9df0145c3
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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