HCID 53248331, compound → HCID 18603236, compound

HRID 1913954Notes

Reaction equation

HRID 1913954 reaction equation
[OH:1][CH2:2][CH2:3]/[CH:4]=[CH:5]/[C@@H:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH:8]([CH3:10])[CH3:9].CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:14]([O:13][C:12]([NH:11][C@@H:6]([CH2:7][CH:8]([CH3:10])[CH3:9])/[CH:5]=[CH:4]/[CH2:3][C:2]([OH:21])=[O:1])=[O:18])([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 2

HCID 53248331HCID 53248331, compoundHCID 131709961Jones' reagent

Product 1

HCID 18603236HCID 18603236, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5) (1.00 g, 3.89 mmol) in acetone (40 mL) at 0° C. was added a freshly prepared solution of Jones Reagent (2.5 M, 3.89 mL, 9.71 mmol) and the reaction was stirred at 0° C. for 1 h. The dark solution was extracted with Et2O (3×50 mL), the organic layers washed with water (2×75 mL), brine (1×50 mL), dried (Na2SO4), filtered and concentrated to yield 990 mg (94% crude) of acid (6) as a yellow oil that was used without further purification.

Workup

  1. extractionThe dark solution was extracted with Et2O (3×50 mL)
  2. washthe organic layers washed with water (2×75 mL), brine (1×50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6dc1bfd01ae340fe9236cbe179ed07eb
Source dataset
uspto-grants-2013_12
Patent number
US08609850B2

Reaction notes

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