Triethylsilane → HCID 20592656, compound

HRID 2359281Notes

Reaction equation

HRID 2359281 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:8](O)[CH3:9])[CH:7]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH2:8][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 580463561-(5-chloro-2-methoxyphenyl)ethan-1-ol

Product 1

HCID 20592656HCID 20592656, compoundYield 141.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(5-Chloro-2-methoxyphenyl)ethanol (Preparation 4, 6.97 g, 37.3 mmol), was dissolved in trifluoroacetic acid (20 mL). Triethylsilane (29.8 mL, 187 mmol) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate and washed with water. The organic phase was separated and concentrated in vacuo to afford the title compound (9 g, 141%, contains residual triethylsilane). This material was taken on crude in subsequent steps.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic phase was separated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0139887bd0eb47c99a73089891e35f8b
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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