p-Toluenesulfonic acid → HCID 59354801, compound

HRID 1425871Notes

Reaction equation

HRID 1425871 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[C:12]#[C:13][C:14]([CH3:21])([O:16][Si](C)(C)C)[CH3:15])=[CH:7][C:4]=1[C:5]#[N:6].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[OH:16][C:14]([CH3:21])([CH3:15])[C:13]#[C:12][C:11]([C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[C:5]#[N:6])=[O:22]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 593548212-Methoxy-5-(4-methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile

Product 1

HCID 59354801HCID 59354801, compoundYield 122.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methoxy-5-(4-methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile (1.2 g, 3.01 mmol) in DCM (20 mL) was added PTSA (1.08 g, 5.60 mmol) at RT. The reaction mixture was stirred for 30 minutes and diluted with water (5 mL). The combined organic layers were then washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered, and then concentrated in vacuo to afford 5-(4-hydroxy-4-methylpent-2-ynoyl)-2-methoxybenzonitrile (0.9 g, 97%) as a semi-solid.

Workup

  1. washThe combined organic layers were then 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-22279e16f7124c0c89e5aeae4d66b048
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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