Triethylamine → 4-(Tetrahydro-2H-pyran-3-yl)butyl methanesulfonate
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:2]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)(=[O:22])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(tetrahydro-2H-pyran-3-yl)-1-butanol (1.20 g) in dry dichloromethane (30.3 ml), cooled to 0° C., was added triethylamine (2.43 ml) and methanesulphonyl chloride (0.77 ml) to give a yellow solution. The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate (25 ml). The organic layer was separated, dried by passing through a hydrophobic frit and concentrated in vacuo to afford a yellow oil (1.80 g). The product was purified by silica chromatography using a gradient elution of 0-40% ethyl acetate/cyclohexane to afford the title compound as a yellow oil (1.58 g).
Workup
- customto give a yellow solution
- washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate (25 ml)
- customThe organic layer was separated
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-85536f0c109a4d45a1d1e6b13aa6ff81
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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