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

HRID 1924824Notes

Reaction equation

HRID 1924824 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-250e9f5a16d241d39bb677b2478594d3
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

Loading…