3-Methyl-3-phenylbutan-2-one → HCID 86703986, compound

HRID 1773907Notes

Reaction equation

HRID 1773907 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](=[O:5])[CH3:4].OC1C([O:21][S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])=C(I)C=CC=1>C(#N)C>[CH3:6][C:2]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([CH3:1])[C:3](=[O:5])[CH2:4][O:24][S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:21])=[O:23]

Participants

4

Reactant 2

HCID 2854623-Methyl-3-phenylbutan-2-oneHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 86703986HCID 86703986, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-methyl-3-phenyl-butan-2-one (example 207D) (8.7 g, 53.6 mmoles) in ACN (150 mL) is added hydroxy(tosyloxy)iodobenzene (22.1 g, 56.3 mmoles). The reaction mixture is heated at reflux for 5 hours. Solvent and volatiles are removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (heptane:AcOEt) (90:1) to give toluene-4-sulfonic acid 3-methyl-2-oxo-3-phenyl-butyl ester.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. customSolvent and volatiles are removed under reduced pressure
  4. customThe residue is purified by silica gel chromatography
  5. washeluting with (heptane:AcOEt) (90:1)

Sources & evidence

ORD record
ord-4e4bd83700274fa5bdd81d0717f98713
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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