Acetic Acid → (2-Acetylthiazol-4-yl)methyl acetate

HRID 1178200Notes

Reaction equation

HRID 1178200 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:8](=[O:10])[CH3:9])[S:6][CH:7]=1.[C:11]([OH:14])(=[O:13])[CH3:12].C([O-])(=O)C.[K+]>C(OCC)(=O)C>[C:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:2][O:14][C:11](=[O:13])[CH3:12])[N:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 692875611-(4-Bromomethyl-thiazol-2-yl)-ethanone

Product 1

HCID 69288714(2-Acetylthiazol-4-yl)methyl acetateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Bromide 3a (4.95 g, 0.0224 mol) was heated with acetic acid (50 mL) and potassium acetate (2.64 g, 0.0269 mol) at 100° C. for 16 h. Diluted with ethyl acetate and washed with water 3 times. The organic layer was dried (Na2SO4) and concentrated in vacuo to give a crude oil that was subjected to flash chromatography (20% ethyl acetate/80% hexanes) to give 2.48 g (70%) of the desired product 4a. 1H NMR (CDCl3) δ 7.8 (s, 1H), 5.2 (s, 2H), 2.8 (s, 3H), 2.2 (s, 3H).

Workup

  1. washwashed with water 3 times
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a crude oil that

Sources & evidence

ORD record
ord-db4cb784d74949e89c77ddbd6f5facc2
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

Loading…