Acetone → HCID 86733394, compound

HRID 1076056Notes

Reaction equation

HRID 1076056 reaction equation
[C:1]([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[CH:6]=[CH:7]/[C@@H:8]1[C@@H:12]([CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:11]=[CH:10][CH:9]1[OH:23])(=[O:3])[CH3:2].CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>O>[C:1]([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[CH:6]=[CH:7]/[C@@H:8]1[C@@H:12]([CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:11]=[CH:10][C:9]1=[O:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 86733393HCID 86733393, compoundHCID 131709961Jones' reagent

Product 1

HCID 86733394HCID 86733394, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

to a solution of 26 parts of methyl (5Z,13E,15S)-15-acetyloxy-11ξ-hydroxyprosta-5,9,13-trien-1-oate in 200 parts of acetone at -10° is added 100 parts of Jones reagent. The resultant mixture is stirred at -10° for 7 minutes, then diluted with 10 volumes of water. The mixture thus obtained is extracted with dichloromethane. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The oily residue is taken up in benzene; and the benzene solution is chromatographed on silica gel, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvent. From an eluate comprising 5% ethyl acetate in benzene, on evaporation of solvent, methyl (5Z,13E,15S)-15-acetyloxy-11-oxoprosta-5,9,13-trien-1-oate is obtained as a pale yellow oil. The product has the formula ##SPC3##

Workup

  1. customThe mixture thus obtained
  2. extractionis extracted with dichloromethane
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation
  6. customand the benzene solution is chromatographed on silica gel
  7. customFrom an eluate comprising 5% ethyl acetate in benzene, on evaporation of solvent

Sources & evidence

ORD record
ord-a2485e133b1545bf89fba483ff311cd8
Source dataset
uspto-grants-1976_05
Patent number
US03954844

Reaction notes

Loading…