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

HRID 1698187Notes

Reaction equation

HRID 1698187 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-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-bromo-thiazol-5-yl)-propan-1-ol (180 mg, 0.79 mmol) in dichloromethane (10 mL) was added Dess-Martin periodinane (DMP) (330 mg, 0.79 mmol). The reaction was stirred for 2 hours, then diluted with dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated. The compound was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford 1-(2-bromo-thiazol-5-yl)-propan-1-one.

Workup

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

Sources & evidence

ORD record
ord-9800a98945dc407dac394c0fe70fcdb7
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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