Ethyl Acetate → HCID 15922633, compound

HRID 1374612Notes

Reaction equation

HRID 1374612 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=[O:26])C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:26])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15922632HCID 15922632, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15922633HCID 15922633, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

6.1 g of 2-(5-fluoro-2-methylphenyl)-2-methylpropionitrile, dissolved in 60 ml of toluene, is mixed at −70° C. for 45 minutes with 44 ml of 1.2 M diisobutylaluminum hydride solution in toluene. After 4 hours at −78° C., 120 ml of ethyl acetate is added in drops. It is heated to room temperature and washed three times with 2N sulfuric acid and once with water. The ethyl acetate phase is dried (Na2SO4) and concentrated by evaporation. After distillation, 5.3 g of 2-(5-fluoro-2-methylphenyl)-2-methylpropionaldehyde of boiling point 120° C./0.031 hPa is obtained.

Workup

  1. washwashed three times with 2N sulfuric acid
  2. dry with materialThe ethyl acetate phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. distillationAfter distillation, 5.3 g of 2-(5-fluoro-2-methylphenyl)-2-methylpropionaldehyde of boiling point 120° C./0.031 hPa
  5. customis obtained

Sources & evidence

ORD record
ord-73ac8404daf343fa9dd1b6c5ffd7ba52
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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