Triethylamine → 3-(2-Propoxyphenyl)propyl methanesulfonate

HRID 1169489Notes

Reaction equation

HRID 1169489 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][CH2:13][OH:14])[CH2:2][CH3:3].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1.C(OCC)(=O)C>[CH3:22][S:23]([O:14][CH2:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:1][CH2:2][CH3:3])(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 229900333-(2-Propoxyphenyl)-1-propanol

Product 1

HCID 229899923-(2-Propoxyphenyl)propyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 3-(2-propoxyphenyl)-1-propanol (729 mg) dissolved in THF (35 ml) were added at 0° C. triethylamine (1.57 ml) and methanesulfonyl chloride (0.44 ml). The resulting mixture was stirred at 0° C. for 20 minutes and at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and was washed respectively with water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-(2-propoxyphenyl)propyl methanesulfonate (1.06 g) as a colorless oil.

Workup

  1. washwas washed respectively with water
  2. dry with materialan aqueous saturated solution of sodium chloride, and the organic layer was dried with magnesium sulfate
  3. customThe resulting organic layer was evaporated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-53d7f5ee16d54033af3d34487a317257
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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