Triacetoxyperiodinane → 1-(2-Bromothiazol-5-yl)propan-1-one

HRID 2067988Notes

Reaction equation

HRID 2067988 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:7]([OH:10])[CH2:8][CH3:9])=[CH:5][N:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 584433781-(2-Bromo-thiazol-5-yl)-propan-1-ol

Product 1

HCID 592780851-(2-Bromothiazol-5-yl)propan-1-oneYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-Bromo-thiazol-5-yl)-propan-1-ol (175 mg, 0.79 mmol) in dichloromethane (10 mL) was added Dess-Martin periodinane (334 mg, 0.79 mmol). The reaction was stirred for 2 h, then diluted with dichloromethane (50 mL), washed with sat. sodium bicarbonate solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes gave 1-(2-bromo-thiazol-5-yl)-propan-1-one (75 mg, 43%).

Workup

  1. washwashed with sat. sodium bicarbonate solution (50 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography
  6. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2ea53f792e364856acf6b38f594545b9
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

Loading…