1-[3-(Trifluoromethyl)phenyl]but-1-en-3-one → HCID 61748346, compound

HRID 1925537Notes

Reaction equation

HRID 1925537 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17](=[O:19])[CH3:18])[CH:12]=[CH:13][CH:14]=1>C1COCC1>[F:7][C:8]([F:20])([F:21])[C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH:17]([OH:19])[CH3:18])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 1449341-[3-(Trifluoromethyl)phenyl]but-1-en-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 61748346HCID 61748346, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

590 mg (15.4 mmol) of LiAlH4 were added in portions at 0° C. to a solution of 2.2 g (10.3 mmol) of 4-(3-(trifluoromethyl)phenyl)but-3-en-2-one in THF (20 ml), and stirring was then carried out for 1 h at RT. The mixture was then quenched at 0° C. with a sat. aq. Na2SO4 sol. and the reaction solution was filtered over kieselguhr. The filtrate was extracted with EA (3×60 ml) and the combined organic phases were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. There were obtained as residue 2.0 g (9.2 mmol, 89%) of 4-(3-(trifluoromethyl)phenyl)-butan -2-ol, which was reacted further without additional purification.

Workup

  1. customThe mixture was then quenched at 0° C. with a sat. aq. Na2SO4 sol.
  2. filtrationthe reaction solution was filtered over kieselguhr
  3. extractionThe filtrate was extracted with EA (3×60 ml)
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0246f0a5cefd47308c72efa608edbac3
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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