Potassium Hydroxide → HCID 22734247, compound

HRID 1057904Notes

Reaction equation

HRID 1057904 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:30])[C:7]=1[CH2:8][C:9]([C:11]1[C:16]2[CH:17]=[C:18]([CH:20]([OH:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:19][C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH-].[K+]>CC(C)=O>[C:20]([C:18]1[O:19][C:15]2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=[C:11]([C:9](=[O:10])[CH2:8][C:7]3[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=3[Cl:30])[C:16]=2[CH:17]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 86585823HCID 86585823, compoundHCID 131709961Jones' reagent

Product 1

HCID 22734247HCID 22734247, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 164a (1.0 g) obtained in Step A was dissolved in acetone (200 ml) and 2.67M Jones' reagent (1.0 ml) was added thereto, followed by stirring at room temperature for 10 minutes. A 1N aqueous solution of potassium hydroxide was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was triturated with diethyl ether to give Compound 164 (0.66 g, 66.5%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-0b3c5c54189e40fcbb928c9c7ac4880b
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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