p-Toluenesulfonic acid → 4-(4-Hydroxy-4-methylpent-2-ynoyl)benzonitrile

HRID 1258308Notes

Reaction equation

HRID 1258308 reaction equation
[CH3:1][C:2]([O:16][Si](C)(C)C)([CH3:15])[C:3]#[C:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[OH:16][C:2]([CH3:15])([CH3:1])[C:3]#[C:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=1)=[O:6]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 666439704-(4-Methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile

Product 1

HCID 666439664-(4-Hydroxy-4-methylpent-2-ynoyl)benzonitrileYield 112.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile (1.7 g, 5.00 mmol) in DCM (15 mL) was added PTSA (1.70 g, 8.90 mmol) at RT and the reaction mixture was stirred for 30 min. The reaction mixture was diluted with water (10 mL) and extracted with DCM (2×50 mL). The combined organic layers were washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered, and then concentrated in vacuo to afford 4-(4-hydroxy-4-methylpent-2-ynoyl)benzonitrile (1.20 g) as a yellow oil.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined organic layers were washed with a saturated NaHCO3 solution and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-468c494110d7441a99c2ad220b6f8e4f
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

Loading…