p-Toluenesulfonic acid → HCID 59354791, compound

HRID 1776375Notes

Reaction equation

HRID 1776375 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[O:20])[C:8]#[C:9][C:10]2([O:15][Si](C)(C)C)[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:3][CH:2]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[OH:15][C:10]1([C:9]#[C:8][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[O:20])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59354815HCID 59354815, compound

Product 1

HCID 59354791HCID 59354791, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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 3-(1-hydroxycyclopentyl)-1-(pyridin-4-yl)prop-2-yn-1-one (0.42 g, 51%) 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-875f5e7cfb6946d6b0f26d92f26cc74d
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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