p-Toluenesulfonic acid → HCID 59354863, compound

HRID 655482Notes

Reaction equation

HRID 655482 reaction equation
[CH3:1][C:2]([O:13][Si](C)(C)C)([CH3:12])[C:3]#[C:4][C:5]([C:7]1[N:8]=[CH:9][S:10][CH:11]=1)=[O:6].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[OH:13][C:2]([CH3:12])([CH3:1])[C:3]#[C:4][C:5]([C:7]1[N:8]=[CH:9][S:10][CH:11]=1)=[O:6]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 593548254-Methyl-1-(thiazol-4-yl)-4-(trimethylsilyloxy)pent-2-yn-1-one

Product 1

HCID 59354863HCID 59354863, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-methyl-1-(thiazol-4-yl)-4-(trimethylsilyloxy) pent-2-yn-1-one (0.15 g, 0.56 mmol) in DCM (3 mL) was added PTSA (0.16 g, 0.84 mmol) at RT and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with water (10 mL), the organic layer was washed with a saturated NaHCO3 solution, water, dried over Na2SO4, filtered and then concentrated in vacuo to afford 4-hydroxy-4-methyl-1-(thiazol-4-yl) pent-2-yn-1-one (0.12 g, crude) as an oil.

Workup

  1. washthe organic layer was washed with a saturated NaHCO3 solution, water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b67a0d4288f4b91a2f420868452b509
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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