p-Toluenesulfonic acid → HCID 65576863, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[O:20])[C:8]#[C:9]C2(O[Si](C)(C)C)CCCC2)=[CH:3][CH:2]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[O:20])[C:8]#[CH:9])=[CH:3][CH:2]=1Participants
5
Procedure
To a stirred solution of 1-(pyridin-4-yl)-3-(1-(trimethylsilyloxy)cyclopentyl) prop-2-yn-1-one (1.1 g, 3.8 mmol) in DCM (15 mL) was added PTSA (0.87 g, 4.6 mmol) at RT and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (2 mL), the organic layer was washed with a saturated NaHCO3 solution, water, dried over Na2SO4, filtered and then concentrated in vacuo to afford 341-hydroxycyclopentyl)-1-(pyridin-4-yl) prop-2-yn-1-one (0.42 g, 51%) as an oil.
Workup
- washthe organic layer was washed with a saturated NaHCO3 solution, water
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c104358ab89c4a2b8d9bdb9e4fd4d0f3
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071595B2
Reaction notes
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