p-Toluenesulfonic acid → 4-Hydroxy-4-methyl-1-(pyridin-4-yl)pent-2-yn-1-one

HRID 1842389Notes

Reaction equation

HRID 1842389 reaction equation
[CH3:1][C:2]([O:14][Si](C)(C)C)([CH3:13])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:6].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[OH:14][C:2]([CH3:13])([CH3:1])[C:3]#[C:4][C:5]([C:7]1[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 593547674-Methyl-1-(pyridin-4-yl)-4-(trimethylsilyloxy)pent-2-yn-1-one

Product 1

HCID 593548164-Hydroxy-4-methyl-1-(pyridin-4-yl)pent-2-yn-1-oneYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-methyl-1-(pyridin-4-yl)-4-(trimethylsilyloxy) pent-2-yn-1-one (0.5 g, 1.915 mmol) in DCM (10 mL) was added PTSA (0.47 g, 2.49 mmol) at RT and the reaction mixture was stirred for 2 h. The reaction mixture was diluted with DCM (50 mL). The organic layers were washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered and then concentrated in vacuo to afford 4-hydroxy-4-methyl-1-(pyridin-4-yl) pent-2-yn-1-one (0.35 g, 96%) as an oil.

Workup

  1. washThe organic layers were washed with a saturated NaHCO3 solution and water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d240d8f3085e46f4821d87f273d6ae16
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

Loading…