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

HRID 1423039Notes

Reaction equation

HRID 1423039 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) is added Dess-Martin periodinane (DMP) (330 mg, 0.79 mmol). After 2 hours, the mixture is diluted with dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over sodium sulfate, filtered and concentrated. The mixture is purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 1-(2-bromo-thiazol-5-yl)-propan-1-one.

Workup

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

Sources & evidence

ORD record
ord-526061e6b0c1402f8088a5e52dce10e0
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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