Methyl iodide → 2-(2-Methoxybut-3-yn-2-yl)-1,3-thiazole

HRID 1398511Notes

Reaction equation

HRID 1398511 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:10])([C:8]#[CH:9])[CH3:7].[H-].[Na+].[CH3:13]I>CN(C=O)C>[CH3:13][O:10][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([C:8]#[CH:9])[CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 582215512-(Thiazol-2-yl)but-3-yn-2-ol

Product 1

HCID 866695722-(2-Methoxybut-3-yn-2-yl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (I-1) (1.0 g, 6.33 mmol) in DMF (15 mL) cooled to 0° C., was slowly added sodium hydride (60% oil dispersion) (0.30 g, 7.6 mmol). After stirring at 0° C. for 20 min, methyl iodide (0.47 mL, 7.6 mmol) was added. The solution was warmed to RT. The mixture was partition between EtOAc (50 mL) and water (20 mL). The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (Isolute column, 20% EtOAc in heptane) gave the title compound as a pale yellow oil: 1H NMR (250 MHz, CDCl3) δ 1.91 (3H, s), 2.78 (1H, s), 3.41 (3H, s), 7.35 (1H, d, J=3.20 Hz), 7.80 (1H, d, J=3.20 Hz); LC-MS: m/z=+167.9 (M+H)+.

Workup

  1. temperatureThe solution was warmed to RT
  2. customThe mixture was partition between EtOAc (50 mL) and water (20 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (Isolute column, 20% EtOAc in heptane)

Sources & evidence

ORD record
ord-421bba137cc54a4eb7b1ced23481b114
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…