HCID 19088069, compound → HCID 19088076, compound

HRID 1464501Notes

Reaction equation

HRID 1464501 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]1[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([CH3:23])[C:17](=[O:24])[C:16]=1[CH:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:26][CH2:27][CH2:28][C:29]#[C:30][CH2:31][OH:32]>CC(C)=O>[CH3:14][C:15]1[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([CH3:23])[C:17](=[O:24])[C:16]=1[CH:25]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:26][CH2:27][CH2:28][C:29]#[C:30][C:31]([OH:3])=[O:32]

Participants

4

Reactant 2

HCID 19088069HCID 19088069, compoundHCID 131709961Jones' reagent

Product 1

HCID 19088076HCID 19088076, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (2.25 ml) was added dropwise to a solution of 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenyl-2-heptyne-1-ol (1.01 g, 3.0 mmole) in acetone (15 ml) at room temperature over the 15-minutes period. The mixture was stirred at room temperature for another 30 minutes and the acetone was distilled off under reduced pressure. Isopropyl ether and water were added to the residue, and extraction was effected. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residue was recrystallized from isopropyl ether to give 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenyl-2-heptynoic acid (0.71 g, 68%).

Workup

  1. distillationthe acetone was distilled off under reduced pressure
  2. additionIsopropyl ether and water were added to the residue, and extraction
  3. customThe isopropyl ether layer was separated out
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-bf8a2a023a5742b5868cd6aebb5e6e6f
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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