Water → HCID 66898038, compound

HRID 1631879Notes

Reaction equation

HRID 1631879 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH:9]2[CH2:13][CH:12]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:10]2=[O:30])[CH2:4][CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[O:30]=[C:10]1[CH:9]([CH2:8][CH:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)[CH2:13][CH:12]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]1[C:21]1[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 66867975HCID 66867975, compoundHCID 131709961Jones' reagent

Product 1

HCID 66898038HCID 66898038, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

The 2,2-dimethyl-propionic acid 4-(4-hydroxy-cyclohexylmethyl)-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (100 mg) is dissolved in acetone and cooled to 0° C. The Jones reagent (1.3 ml, 167 M) is added dropwise over a period of 30 minutes. The reaction is allowed to warm to room temperature over 1 hour. The reaction is poured into water and extracted with ethyl acetate (3×50 ml). The combined organic extracts are washed with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure to give a white crystalline solid. The solid is purified by flash chromatography to give the 2,2-dimethyl-propionic acid 3-oxo-4-(4-oxo-cyclohexylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (72 mg).

Workup

  1. temperatureto warm to room temperature over 1 hour
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic extracts are washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customto give a white crystalline solid
  8. customThe solid is purified by flash chromatography

Sources & evidence

ORD record
ord-e1d7b408655c458eb7f04e2323848ac7
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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