Isopropanol → HCID 15003279, compound

HRID 1199850Notes

Reaction equation

HRID 1199850 reaction equation
[O:1]([CH:8]([CH3:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14](C)=[O:15].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[O:1]([CH:8]([CH3:12])[CH2:9][C:10]([O:15][CH2:14][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 15003276HCID 15003276, compoundHCID 131709961Jones' reagent

Product 1

HCID 15003279HCID 15003279, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.15 g of the crude alcohol 27 (prepared in 30-(3)) in 80 ml of acetone is added 10 ml of 8N Jones' reagent at 20° C. to 30° C. dropwise. The mixture is stirred for additional 10 minutes, and 3 ml of isopropyl alcohol is added thereto. The resulting mixture is stirred for 10 minutes and acetone is evaporated under reduced pressure. Water is added to the residue, and the residue is extracted with ethyl acetate twice. The organic layer is washed with water and then extracted with 1N aqueous solution of sodium hydroxide. The aqueous layer is acidified to pH 2 with hydrochloric acid and extracted with ethyl acetate again. The ethyl acetate extract is washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue is dissolved in 50 ml of ether and an ethereal solution of diazoethane is added at 0° C. until the orange color persists. The reaction mixture is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel (50 of silica gel, ethyl acetate-n-hexane=1:19) to give 2.35 g of the desired ethyl ester 28 as an oil in 67.0% yield from the compound 26.

Workup

  1. stirringThe resulting mixture is stirred for 10 minutes
  2. customacetone is evaporated under reduced pressure
  3. additionWater is added to the residue
  4. extractionthe residue is extracted with ethyl acetate twice
  5. washThe organic layer is washed with water
  6. extractionextracted with 1N aqueous solution of sodium hydroxide
  7. extractionextracted with ethyl acetate again
  8. extractionThe ethyl acetate extract
  9. washis washed with water
  10. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. dissolutionThe residue is dissolved in 50 ml of ether
  13. additionan ethereal solution of diazoethane is added at 0° C. until the orange color persists
  14. customThe reaction mixture is evaporated under reduced pressure
  15. customthe residue is purified by column chromatography on silica gel (50 of silica gel, ethyl acetate-n-hexane=1:19)

Sources & evidence

ORD record
ord-3650c7ebcdcc4bc7abff2ce1b578d656
Source dataset
uspto-grants-1990_02
Patent number
US04902811

Reaction notes

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