Methanol → HCID 57804217, compound

HRID 2102900Notes

Reaction equation

HRID 2102900 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13]C)=[O:12])=[N:9][CH:10]=1.[OH-].[Li+].CO>O>[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 69063586HCID 69063586, compound

Product 1

HCID 57804217HCID 57804217, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL round bottom flask was added methyl 5-(3,3-dimethylbut-1-ynyl)picolinate (4.5 g, 21 mmol), lithium hydroxide (5.02 g, 210 mmol), methanol (80 mL), and water (30 mL). The mixture was stirred at room temperature for 30 minutes, heated to reflux for 1 hour, then concentrated under vacuum. Water (100 mL) was added and the mixture was cooled to 0° C. Concentrated HCl was added slowly to the stirred solution until the pH of the solution reached 6. An off white precipitate formed and was filtered, washed with cold water (3×100 mL) and dried under vacuum to afford the product (3.97 g, 95%) as an off white solid. LC-MS 2.76 min, 202.9 (M−1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated under vacuum
  4. additionWater (100 mL) was added
  5. temperaturethe mixture was cooled to 0° C
  6. additionConcentrated HCl was added slowly to the stirred solution until the pH of the solution
  7. customAn off white precipitate formed
  8. filtrationwas filtered
  9. washwashed with cold water (3×100 mL)
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7b9af030818041bc9a84c30b9f0dcf4f
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

Loading…