Triethylamine → 2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

HRID 985500Notes

Reaction equation

HRID 985500 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:15][CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:2]=1[CH3:1])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(5-Methyl-2-phenyloxazol-4-yl)ethanol (20 g) and triethylamine (19.2 ml) were added to methylene chloride (200 ml) and, after dropwise addition of methanesulfonyl chloride (9.52 ml) at 0° C., the mixture was stirred at the same temperature for 15 min. The reaction mixture was washed with 10% aqueous citric acid solution (200 ml), saturated aqueous sodium hydrogen carbonate (100 ml) and saturated brine (100 ml), and dried (Na2SO4). Methylene chloride was evaporated under reduced pressure and the obtained residue was purified by column chromatography to give the title compound (21.45 g). 1H-NMR (CDCl3) δ (ppm); 2.53 (3H, s), 2.94 (3H, s), 2.94 (2H, t, J=7.0 Hz), 4.52 (2H, t, J=7.0 Hz), 7.30-7.50 (3H, m), 7.80-8.10 (2H, m).

Workup

  1. washThe reaction mixture was washed with 10% aqueous citric acid solution (200 ml), saturated aqueous sodium hydrogen carbonate (100 ml) and saturated brine (100 ml)
  2. dry with materialdried (Na2SO4)
  3. customMethylene chloride was evaporated under reduced pressure
  4. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-eea28222028d48dc8042cb1dfe31a9e4
Source dataset
uspto-grants-2005_03
Patent number
US06872732B2

Reaction notes

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