Isopropanol → HCID 19966472, compound

HRID 1756342Notes

Reaction equation

HRID 1756342 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:17][CH:18]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26](/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[CH:34]([O:43][C:44](=[O:46])[CH3:45])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:25]=1)[CH2:19][CH2:20][CH2:21][CH:22]=[O:23])(=[O:16])[CH3:15].C(O)(C)C>CC(C)=O.CCOCC>[C:14]([O:17][CH:18]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26](/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[CH:34]([O:43][C:44](=[O:46])[CH3:45])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:25]=1)[CH2:19][CH2:20][CH2:21][C:22]([OH:3])=[O:23])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 19966470HCID 19966470, compoundHCID 131709961Jones' reagent

Product 1

HCID 19966472HCID 19966472, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

0.3 ml of Jones reagent (J. Chem. Soc. 1953, 2555) is instilled in a solution of 150 mg of the above-produced aldehyde in 11 ml of acetone with stirring at -30° C. and stirred for one hour at -30° C. Then, 0.23 ml of isopropanol is added, stirred for 15 minutes, diluted with ether, filtered, washed neutral with brine, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/0-50% ethyl acetate, 52 mg of (5RS)-5-acetoxy-5-{3-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl)-pentanoic acid is obtained as colorless oil.

Workup

  1. stirringstirred for one hour at -30° C
  2. stirringstirred for 15 minutes
  3. filtrationfiltered
  4. washwashed neutral with brine
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-8cc8992034f548aea230bb9aaa79d41b
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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