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

HRID 559688Notes

Reaction equation

HRID 559688 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-f0a70ef8f5b24a7eb12ff8b696b22c36
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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