Triphenylphosphine → Methyl 5-(but-2-yn-1-yloxy)picolinate

HRID 1770885Notes

Reaction equation

HRID 1770885 reaction equation
[CH2:1]([OH:5])[C:2]#[C:3][CH3:4].O[C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[N:11][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([O:5][C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[N:11][CH:12]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 129912-Butyn-1-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 58449213Methyl 5-(but-2-yn-1-yloxy)picolinateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of but-2-yn-1-ol (0.635 mL, 8.49 mmol) in THF (30 mL) were added methyl 5-hydroxypicolinate (1.3 g, 8.49 mmol), triphenylphosphine (3.34 g, 12.73 mmol) and diisopropyl azodicarboxylate (2.507 mL, 12.73 mmol) at 0° C. The reaction mixture was then allowed to reach r.t and stirred for 2 days. The reaction mixture was concentrated and the product was purified by flash chromatography using a heptane/EtOAc gradient to give 1.42 g (82% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.87 (t, 3H), 4.00 (s, 3H), 4.79 (q, 2H), 7.41 (dd, 1H), 8.11-8.20 (m, 1H), 8.49 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-6d1a661dac7f4b01b54d6f650d750031
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

Loading…