HCID 11524070, compound → HCID 9821973, compound

HRID 1057893Notes

Reaction equation

HRID 1057893 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][CH:9]([C:11]1[C:16]2[O:17][C:18]3([O:23][C:15]=2[C:14]([O:24][CH3:25])=[CH:13][CH:12]=1)[CH2:22][CH2:21][CH2:20][CH2:19]3)[OH:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C:9]([C:11]1[C:16]2[O:17][C:18]3([O:23][C:15]=2[C:14]([O:24][CH3:25])=[CH:13][CH:12]=1)[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:10]

Participants

4

Reactant 2

HCID 11524070HCID 11524070, compoundHCID 131709961Jones' reagent

Product 1

HCID 9821973HCID 9821973, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 138a (2.88 g) obtained in Step A was dissolved in acetone (200 ml) and 2.67M Jones' reagent (3.0 ml) was added thereto, followed by stirring at 0° C. for 15 minutes. The reaction solution was concentrated to about a half by volume, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10 to 5/1) to give Compound 140 (2.02 g, 70%) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated to about a half by volume, and water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10 to 5/1)

Sources & evidence

ORD record
ord-9145bc593b324f07bbfbc597e5379ca4
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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