Water → (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propen-1-ol

HRID 496047Notes

Reaction equation

HRID 496047 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]([F:27])([F:26])[C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)/[CH:16]=[CH:17]/[C:18](OCC)=[O:19].O>C1COCC1>[F:11][C:12]([F:26])([F:27])[C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)/[CH:16]=[CH:17]/[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 962WaterHCID 10562229HCID 10562229, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19773124(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propen-1-olYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

12.29 ml of 1M diisobutylaluminum hydride solution in THF diluted with 20 ml of THF are introduced under argon and a solution of 1.00 g (4.095 mmol) of ethyl E-3-trifluoromethylcinnamate in 20 ml of THF is added dropwise. The mixture is subsequently stirred for 30 min, hydrolyzed with water, then extracted with dichloromethane, and the combined extracts are dried and concentrated. Column chromatography on silica gel (mobile phase:cyclohexane:ethylacetate:=7:3) yields in the first fraction 420 mg (50.7% of theory) of E-3-trifluoromethylcinnamyl alcohol which is employed further for the oxidation.

Workup

  1. additionare introduced under argon
  2. extractionextracted with dichloromethane
  3. customthe combined extracts are dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d34170d1be574046ae803818b56b3547
Source dataset
uspto-grants-2005_09
Patent number
US06943182B2

Reaction notes

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