Sodium Hydroxide → 5-Ethynyl-2,3-dimethoxypyridine

HRID 709047Notes

Reaction equation

HRID 709047 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]#[C:12][Si](C)(C)C)=[CH:5][N:4]=1.[OH-].[Na+]>CO>[C:11]([C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1)#[CH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 467378382,3-Dimethoxy-5-[2-(trimethylsilyl)ethynyl]pyridine2×

Product 1

HCID 582133895-Ethynyl-2,3-dimethoxypyridineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Dimethoxy-5-[(trimethylsilyl)ethynyl]pyridine (Intermediate 31) (9.8 g, 42 mmol) was dissolved in a mixture of aqueous sodium hydroxide (21 ml, 2 M, 42 mmol) and methanol (50 ml) to give a colourless solution which was stirred for 16 hours. The reaction was evaporated and the residue was partitioned between ethyl acetate and water before the organic layer was dried and concentrated in vacuo. The crude material was purified by (SiO2; 0-10% ethyl acetate in petrol) to afford 5-ethynyl-2,3-dimethoxypyridine (5.6 g, 82%).

Workup

  1. customto give a colourless solution which
  2. customThe reaction was evaporated
  3. customthe residue was partitioned between ethyl acetate and water before the organic layer
  4. customwas dried
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by (SiO2; 0-10% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-7a477c5919c743b684e780b8f7c73222
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

Loading…