Triethylamine → Methanesulfonic acid 3-phenyl-prop-2-ynyl ester

HRID 1162521Notes

Reaction equation

HRID 1162521 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C>C(Cl)Cl>[C:1]1([C:7]#[C:8][CH2:9][O:10][S:12]([CH3:11])(=[O:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1231153-Phenyl-2-propyn-1-ol

Product 1

HCID 10584567Methanesulfonic acid 3-phenyl-prop-2-ynyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Phenyl-prop-2-yn-1-ol 37 (3.0 g, 22.7 mmol) is dissolved in DCM (50 mL). The solution is cooled to 0° C., then methanesulfonyl chloride (4.5 mL, 34.1 mmol) and triethyl amine (4.7 mL, 34.1 mmol) is added. The mixture is allowed to warm to room temperature and stirred overnight at room temperature. The mixture is washed with H2O (2×30 mL). The organic layer is dried (MgSO4), filtered, and concentrated to afford crude methanesulfonic acid 3-phenyl-prop-2-ynyl ester 38 as a clear oil: 1H-NMR (400 MHz, CDCl3) δ=7.47-7.32 (m, 5H), 4.38 (s, 2H), 3.67 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. washThe mixture is washed with H2O (2×30 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4af43dc01ab64c53804b5cff9e1b66e2
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

Loading…