Borane → (2-Ethyl-6-methyl-pyridin-4-yl)-methanol

HRID 2366119Notes

Reaction equation

HRID 2366119 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:6](O)=[O:7])[CH3:2].B>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:9]=[C:10]([CH3:12])[N:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 584180972-Ethyl-6-methylisonicotinic acid

Product 1

HCID 67520483(2-Ethyl-6-methyl-pyridin-4-yl)-methanolYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-ethyl-6-methyl-isonicotinic acid (2.73 g, 16.5 mmol) in THF (30 mL) is treated with borane in THF (1M, 33.1 mL) at rt for 15 h. The mixture is quenched with sat. aq. Na2CO3 (100 mL) and extracted with CHCl3 (5×50 mL). The organic extracts are dried (Na2SO4), filtered and evaporated (50 mbar, 45° C.) to give crude (2-ethyl-6-methyl-pyridin-4-yl)-methanol (2.18 g); LC-MS: tR=0.80 min, [M+1]+=205.32.

Workup

  1. customThe mixture is quenched with sat. aq. Na2CO3 (100 mL)
  2. extractionextracted with CHCl3 (5×50 mL)
  3. dry with materialThe organic extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated (50 mbar, 45° C.)

Sources & evidence

ORD record
ord-1fc57dfe5be94e8ba81464b315c4be6d
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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