Acetic Acid → HCID 14649321, compound

HRID 414295Notes

Reaction equation

HRID 414295 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:16]([F:19])([F:18])[F:17])[CH2:11][C:12](OC)=[O:13])=[CH:6][CH:5]=1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:16]([F:17])([F:18])[F:19])[CH2:11][CH:12]=[O:13])=[CH:8][CH:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 14649319HCID 14649319, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14649321HCID 14649321, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl 3-(4-ethoxyphenyl)-4,4,4-trifluorobutanoate (2.0 g, 7.2×10-3 moles) in toluene (25 cm3) at -78° C. was added one molar diisobutylaluminium hydride (7.2 ml, 7.2×10-3 moles) in toluene. The resulting solution was stirred at -78° C. for two hours before quenching the reaction by the sequential addition of acetic acid (0.48 cm3, 8.4×10-3 moles), water (1 cm3) and sodium sulphate (10 g). The resulting slurry was allowed to warm to room temperature and after a further twenty minutes stirring the solids were filtered off through a silica plug. The solvent was removed to leave a colourless oil which was characterised as the title compound.

Workup

  1. custombefore quenching
  2. customthe reaction
  3. temperatureto warm to room temperature and after a further twenty minutes
  4. stirringstirring the solids
  5. filtrationwere filtered off through a silica plug
  6. customThe solvent was removed
  7. customto leave a colourless oil which

Sources & evidence

ORD record
ord-0d5e833f7fe24c06b217200113c335e7
Source dataset
uspto-grants-1988_12
Patent number
US04791139

Reaction notes

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