4-Toluenesulfonyl chloride → 3-Cyclopropylprop-2-ynyl 4-methylbenzenesulfonate
Reaction equation
[CH:1]1([C:4]#[C:5][CH2:6][OH:7])[CH2:3][CH2:2]1.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:15][C:14]1[CH:16]=[CH:17][C:11]([S:8]([O:7][CH2:6][C:5]#[C:4][CH:1]2[CH2:3][CH2:2]2)(=[O:10])=[O:9])=[CH:12][CH:13]=1Participants
6
Procedure
To a stirred solution of crude 3-cyclopropylprop-2-yn-1-ol (intermediate AT) (0.55 mg) in 10 mL of CH2Cl2 was added TsCl (1.33 g, 6.87 mmol) and DMAP (0.035 g, 0.2865 mmol) at 0° C. Triethylamine (0.96 mL, 6.87 mmol) was added dropwise to the mixture and the reaction temperature was held so as not to exceed 0° C. After stirring for 3h, the mixture was quenched with 10 mL of water. The aqueous layer was extracted twice with 20 mL each of CH2Cl2. The organic layer was washed with 20% HCl and water prior to drying over anhydrous Na2SO4. The organic phase was concentrated and the crude product was purified by gel column chromatography to obtain intermediate AU (0.4 g).
Workup
- customto exceed 0° C
- customthe mixture was quenched with 10 mL of water
- extractionThe aqueous layer was extracted twice with 20 mL each of CH2Cl2
- washThe organic layer was washed with 20% HCl and water
- dry with materialto drying over anhydrous Na2SO4
- concentrationThe organic phase was concentrated
- customthe crude product was purified by gel column chromatography
- customto obtain intermediate AU (0.4 g)
Sources & evidence
- ORD record
- ord-219114e134884a6a9685d9b9a7d3b3d8
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106021B2
Reaction notes
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