Hydrochloric Acid → 2-Methyl-2-(pyridin-4-yl)propan-1-ol

HRID 633722Notes

Reaction equation

HRID 633722 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)([CH3:8])[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH3:8][C:2]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)([CH3:1])[CH2:3][OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10750309HCID 10750309, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 134781392-Methyl-2-(pyridin-4-yl)propan-1-olYield 143.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.58 g (7.36 mmol) of ethyl 2-methyl-2-pyrid-4-ylpropionate in 30 mL of THF is cooled to 10° C. When the temperature is reached, 22.08 mL (22.08 mmol) of 1 M diisobutylaluminum hydride solution in toluene are added dropwise. The reaction mixture is allowed to warm to room temperature and is stirred overnight. 1 N hydrochloric acid solution is added to the reaction medium, which is then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 1.60 g of 2-methyl-2-pyrid-4-ylpropan-1-ol, corresponding to the following characteristics:

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-4480bd6b1d954a4ea5e833fc6e1e3e48
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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