Triethylsilane → 4-Chloro-2-(4-ethylbenzyl)phenol

HRID 1092436Notes

Reaction equation

HRID 1092436 reaction equation
[SiH](CC)(CC)CC.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([OH:25])=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)=O)[CH:14]=1.C(S(O)(=O)=O)(F)(F)F>C(O)(C(F)(F)F)=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([OH:25])=[C:13]([CH2:15][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 57741112(5-Chloro-2-hydroxyphenyl)(4-ethylphenyl)methanone

Product 1

HCID 230727454-Chloro-2-(4-ethylbenzyl)phenolYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred 0° C. solution of Et3SiH (2.26 ml, 14.2 mmol) and (5-chloro-2-hydroxyphenyl)(4-ethylphenyl)methanone (1.944 g, 7.08 mmol) in 10 mL of TFA was added CF3SO3H (30 μL) at a rate to keep the temperature at about 0° C. After complete addition, the mixture was warmed to room temperature and stirred overnight at room temperature. After the volatiles were evaporated under reduced pressure, the residue was partitioned in ethyl acetate and water. The organic layer was separated and washed with water, aq Na2CO3, brine then dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (PE:EA=10:1) to give the target compound (1.659 g).

Workup

  1. customat about 0° C
  2. additionAfter complete addition
  3. customAfter the volatiles were evaporated under reduced pressure
  4. customthe residue was partitioned in ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, aq Na2CO3, brine
  7. dry with materialthen dried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (PE:EA=10:1)

Sources & evidence

ORD record
ord-1228703b609f4c5f8ca80315db073c62
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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