Isopropanol → Methyl 5-bromo-2-oxopentanoate

HRID 1906858Notes

Reaction equation

HRID 1906858 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:23])[C:19]([O:21][CH3:22])=[O:20].C(O)(C)C>CC(C)=O.O>[Br:14][CH2:15][CH2:16][CH2:17][C:18](=[O:23])[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 13769948Methyl 5-bromo-2-hydroxypentanoateHCID 131709961Jones' reagent

Product 1

HCID 13769949Methyl 5-bromo-2-oxopentanoateYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Jones' reagent (CrO3 : 9.58 g, H2SO4 : 8.47 ml, H2O: 36.8 ml) was added to a magnetically stirred solution of Part (3) compound (12.53 g, 59.3 mmole) in acetone (150 ml) at room temperature. The addition was controlled to maintain the temperature below 35° C. After the completion of the addition, the reaction was stirred at room temperature for 45 minutes. Isopropyl alcohol (30 ml) was added dropwise and stirred for 30 minutes. The reaction was then diluted with H2O (500 ml) and the products were extracted with CH2Cl2 (1 l.). The CH2Cl2 layer was washed with brine (100 ml×3) and dried over MgSO4. Filtration and evaporation of solvents gave the title compound (11.4 g, 54.5 mmole, 92%) as a colorless liquid.

Workup

  1. additionThe addition
  2. temperatureto maintain the temperature below 35° C
  3. additionAfter the completion of the addition
  4. stirringstirred for 30 minutes
  5. extractionthe products were extracted with CH2Cl2 (1 l.)
  6. washThe CH2Cl2 layer was washed with brine (100 ml×3)
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and evaporation of solvents

Sources & evidence

ORD record
ord-4e2cd350fe7c4d4b8bde57090990c9c2
Source dataset
uspto-grants-1987_03
Patent number
US04654357

Reaction notes

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