Triethylamine → HCID 11051825, compound
Reaction equation
[CH2:1]([OH:5])[C:2]#[C:3][CH3:4].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CCOCC>[CH2:1]([O:5][S:14]([CH3:13])(=[O:16])=[O:15])[C:2]#[C:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Butyne-1-ol (1.4 g, 20 mmol) is dissolved in ether (50 mL) and cooled to 0° C. Triethylamine (3.3 mL, 24 mmol) is added to the solution. Methanesulfonyl chloride (1.6 mL, 22 mmol) is dissolved in ether (5 mL) and added dropwise to the reaction solution. The mixture is stirred for 30 minutes at 0° C., then filtered and concentrated to give crude methanesulfonic acid but-2-ynyl ester 20 (2.96 g, 20 mmol, quant.) as a colorless liquid: 1H-NMR (400 MHz, CDCl3) δ=4.79 (q, J=2.4 Hz, 2H), 3.08 (s, 3H), 1.87 (t, J=2.4 Hz, 3H).
Workup
- additionadded dropwise to the reaction solution
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b1b3edaf26f4427baf3b3fa533ea63da
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820705B2
Reaction notes
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