2-Acetyl-4-methylthiazole → 2-(4-Methyl-1,3-thiazol-2-yl)but-3-yn-2-ol

HRID 1398513Notes

Reaction equation

HRID 1398513 reaction equation
[C:1]([Mg]Br)#[CH:2].[CH3:5][C:6]1[N:7]=[C:8]([C:11](=[O:13])[CH3:12])[S:9][CH:10]=1>O1CCCC1>[CH3:5][C:6]1[N:7]=[C:8]([C:11]([OH:13])([C:1]#[CH:2])[CH3:12])[S:9][CH:10]=1

Participants

4

Reactant 2

HCID 53247972-Acetyl-4-methylthiazoleHCID 178418486HCID 178418486, compound

Product 1

HCID 866695732-(4-Methyl-1,3-thiazol-2-yl)but-3-yn-2-olYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of ethynylmagnesium bromide (0.5 M in THF, 30.6 mL, 15.30 mmol) maintained under nitrogen at −20° C. was added slowly a solution of 1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one (1.8 g, 10.20 mmol, 80%) in tetrahydrofuran (10 mL) over a period of 20 min. The resulting solution was stirred for 3 hr at 20-30° C. and then quenched by the addition of water (20 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1/6) to yield 0.5 g (26%) of the title compound as a yellow solid: LC-MS: m/z=+168 (M+H)+.

Workup

  1. customquenched by the addition of water (20 mL)
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on a silica gel column
  7. washeluted with ethyl acetate/petroleum ether (1/6)

Sources & evidence

ORD record
ord-ecdde511be56437e8c4d14ccdd5f8bf0
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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