Triethylamine → Hex-5-yn-1-yl methanesulfonate
Reaction equation
[C:1]([OH:7])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[S:15](Cl)([CH3:18])(=[O:17])=[O:16]>C(OCC)C.O>[CH3:18][S:15]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])(=[O:17])=[O:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2.3 ml of hexynol 17a, in 15 ml of diethyl ether was added 3 ml of triethyl amine, followed by 1.6 ml of mesyl chloride at 0° C. The mixture was stirred for 1 hr at 0° C., then diluted with 20 ml of water and extracted with diethyl ether. The extract was washed with 1N NaOH, water, dried and concentrated, to give 3.5 g of mesylate 17b as a colorless oil. Rf 0.65 (heptane/acetone 1/1).
Workup
- extractionextracted with diethyl ether
- washThe extract was washed with 1N NaOH, water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e5bb375394aa43cda1fb141ee2e7c3b6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431564B2
Reaction notes
Loading…