Aluminium lithium hydride → (6-(Propan-2-yl)pyridin-2-yl)methanol

HRID 706724Notes

Reaction equation

HRID 706724 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([C:10](OCC)=[O:11])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67974663Ethyl 6-isopropylpicolinate

Product 1

HCID 21874757(6-(Propan-2-yl)pyridin-2-yl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 6-isopropylpicolinate (4.63 g, 24.0 mmol) in THF (50 mL) at 0° C. was added LAH (0.909 g, 24.0 mmol). The cold bath was removed, and the reaction mixture was stirred for 2 hours and quenched carefully with sodium sulfate decahydrate. The reaction mixture was then filtered through Celite® and washed with Et2O (200 mL). The filtrate was concentrated under reduced pressure to give the desired product (86%).

Workup

  1. customThe cold bath was removed
  2. customquenched carefully with sodium sulfate decahydrate
  3. filtrationThe reaction mixture was then filtered through Celite®
  4. washwashed with Et2O (200 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e76d2e5755614fd1aa99783816e263a6
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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