p-Toluenesulfonic acid → HCID 86634960, compound

HRID 1665219Notes

Reaction equation

HRID 1665219 reaction equation
[CH3:1][C:2]1([CH3:21])[C@H:4](/[CH:5]=[C:6](\[CH3:13])/[CH:7]=[N:8][O:9][CH2:10][C:11]#[CH:12])[C@H:3]1[C:14]([O:16]C(C)(C)C)=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:21])[C@H:4](/[CH:5]=[C:6](\[CH3:13])/[CH:7]=[N:8][O:9][CH2:10][C:11]#[CH:12])[C@H:3]1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86634969HCID 86634969, compound

Product 1

HCID 86634960HCID 86634960, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under nitrogen atmosphere, a mixture of 0.46 g of t-butyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-(2-propynyloxyimino)-1-propenyl]cyclopropanecarboxylate, catalytic amount of p-toluenesulfonic acid and 10 ml of toluene was stirred for 3.5 hours under reflux. The reaction mixture was cooled down to room temperature, then, the mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.35 g of (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-(2-propynyloxyimino)-1-propenyl]cyclopropanecarboxylic acid:

Workup

  1. temperatureunder reflux
  2. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-12c24657e1c14d3a92712d6d8708b330
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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