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

HRID 1357054Notes

Reaction equation

HRID 1357054 reaction equation
C(Cl)Cl.[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][CH2:17][OH:18].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(N(CC)CC)C>[CH3:19][S:20]([O:18][CH2:17][CH2:16][C:6]1[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9][C:5]=1[CH3:4])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 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 8471TriethylamineSolvent

Procedure

To methylene chloride (200 ml) were added 2-(5-methyl-2-phenyl-oxazol-4-yl)ethanol (20 g) and triethylamine (19.2 ml). Thereto was dropwise added methanesulfonyl chloride (9.52 ml) at 0° C. and the mixture was stirred at the same temperature for 15 min. The mixture was washed with 10% aqueous citric acid solution (200 ml), saturated aqueous sodium hydrogencarbonate solution (100 ml) and saturated brine (100 ml) and dried over Na2SO4. Methylene chloride was evaporated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (21.45 g).

Workup

  1. customat 0° C.
  2. washThe mixture was washed with 10% aqueous citric acid solution (200 ml), saturated aqueous sodium hydrogencarbonate solution (100 ml) and saturated brine (100 ml)
  3. dry with materialdried over Na2SO4
  4. customMethylene chloride was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-424ac0c3d6d1488ba0a18d8586582d78
Source dataset
uspto-grants-2003_07
Patent number
US06589963B2

Reaction notes

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