Aluminium lithium hydride → (3,5-Diethylpyridin-4-yl)methanol

HRID 630149Notes

Reaction equation

HRID 630149 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:20][CH3:21])[C:14]=1[C:15](OCC)=[O:16])[CH3:8]>C1COCC1>[CH2:20]([C:13]1[CH:12]=[N:11][CH:10]=[C:9]([CH2:7][CH3:8])[C:14]=1[CH2:15][OH:16])[CH3:21]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59589455Ethyl 3,5-diethylpyridine-4-carboxylate

Product 1

HCID 59589408(3,5-Diethylpyridin-4-yl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (0.805 g, 21.22 mmol) in anhydrous THF (20 mL) at 0° C. was added a dropwise a solution of ethyl 3,5-diethylpyridine-4-carboxylate (2.20 g, 10.61 mmol) in THF (30 mL). After stirring for 1 hour, the reaction mixture was slowly quenched with 15% NaOH solution and then diluted with water. Ethyl acetate was added, the mixture was stirred for 10 minutes, and the precipitated white solid was filtered off. The solid was washed with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to provide (3,5-diethylpyridin-4-yl)methanol as a thick oil (1.50 g, 86% yield) which was used for the next step without any further purification; 1H NMR (400 MHz, DMSO-d6): δ 1.15 (t, 611), 2.70 (q, 4H), 4.50 (s, 2H), 5.06 (bs, 1H), 8.22 (s, 2H), M+208.5; M+166.2.

Workup

  1. customthe reaction mixture was slowly quenched with 15% NaOH solution
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. stirringthe mixture was stirred for 10 minutes
  5. filtrationthe precipitated white solid was filtered off
  6. washThe solid was washed with ethyl acetate (2×50 mL)
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d7496e3c80ac453ca3e45c2eb5796727
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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