Triethylamine → HCID 59210419, compound

HRID 2243273Notes

Reaction equation

HRID 2243273 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]([OH:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[CH3:21][S:22]([O:13][CH:11]([C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)[CH3:12])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59210402HCID 59210402, compound

Product 1

HCID 59210419HCID 59210419, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a THF solution (35 ml) of 1-(3-methyl-4-nitrophenyl)-ethanol (5.44 g) and triethylamine (3.95 g), a THF solution (10 ml) of methanesulfonyl chloride (3.48 g) was added dropwise at 5° C. over a period of 30 minutes. Further, the mixture was stirred at room temperature for 8 hours. After finishing the reaction, the solvent was distilled off and the residue was dissolved in ethyl acetate (100 ml). It was washed with 2N aqueous solution of hydrochloric acid and saturated aqueous solution of sodium bicarbonate and then dried with anhydrous magnesium sulfate. After distilling off the solvent, the aimed 1-(3-methyl-4-nitrophenyl)-ethyl methanesulfonate (5.80 g) was obtained.

Workup

  1. customthe reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  4. washIt was washed with 2N aqueous solution of hydrochloric acid and saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-6b5c3053cc1c49c9a9f247626c4396ac
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

Loading…