Triethylamine → 3-(4-Pentylphenyl)propyl mesylate

HRID 1072714Notes

Reaction equation

HRID 1072714 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][OH:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C1COCC1>[S:23]([O:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1)(=[O:25])(=[O:24])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223875953-(4-Pentylphenyl)propanol

Product 1

HCID 223874783-(4-Pentylphenyl)propyl mesylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-pentylphenyl)propanol (30.8 g, 149 mmol) and triethylamine (22 ml, 155 mmol) in THF (300 ml) was added mesyl chloride (11.6 ml, 150 mmol) at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the organic layer was concentrated to give the object compound as an oily substance. 42.4 g, (yield 100%)

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate anhydride
  5. concentrationthe organic layer was concentrated
  6. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-c5e90e2b0fab4f7fba9bccd76f5f860d
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

Loading…