HCID 86583786, compound → HCID 59970560, compound

HRID 379931Notes

Reaction equation

HRID 379931 reaction equation
[CH3:1][C:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=[CH:3][C:4](OCC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1]/[C:2](/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1)=[CH:3]\[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 86583786HCID 86583786, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 59970560HCID 59970560, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

After a solution in which 150 mg (0.53 mmol) of ethyl (4E)-3-methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadienoate ((2E)/(2Z)=5/1) as described in Reference example 8 were dissolved in 2 ml of toluene was stirred at 0° C., 0.7 ml (1.06 mmol) of a 1.SM diisobutyl aluminum hydride-toluene solution were added to the solution. After 20 minutes, ice-water was added to the reaction mixture and the mixture was stirred for 10 minutes. The insolubles were removed by filtration using Celite and the filtrate was extracted with ethyl acetate and dried, followed by evaporation of the solvent to obtain an oil. The oil was subjected to column chromatography using 5 g of silica gel and eluted with a mixed solvent of 30 to 40% ethyl acetate-hexane to obtain 90 mg of the title compound as an oil.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe insolubles were removed by filtration
  3. extractionthe filtrate was extracted with ethyl acetate
  4. customdried
  5. customfollowed by evaporation of the solvent
  6. customto obtain an oil
  7. washeluted with a mixed solvent of 30 to 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-e22f7eb148b341e0953f6b2d77b10ea8
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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