HCID 16110498, compound → HCID 16110499, compound

HRID 603410Notes

Reaction equation

HRID 603410 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[OH:14])[CH:2]=[CH2:3]>CCO.[Pd]>[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:7]=[CH:6][C:5]=1[OH:14])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 16110498HCID 16110498, compound

Product 1

HCID 16110499HCID 16110499, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude 2-allyl-4-(trifluoromethyl)phenol from Example 90 was dissolved in EtOH (5 mL), 10% Pd/C (20 mg) was added, and the mixture was stirred under an atmosphere of hydrogen at rt for 2 h. The catalyst was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (EtOAc/hexane (v/v) 1:10). This gave 91 mg (45% over 2 steps) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.00 (t, 3H), 1.68 (m, 2H), 2.61 (t, 2H), 5.14 (br, 1H), 6.80 (d, 1H), 7.32 (d, 1H), 7.36 (s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography (EtOAc/hexane (v/v) 1:10)

Sources & evidence

ORD record
ord-f0690733f5a840f7998e32f58485361f
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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