Triethylsilane → Methyl 2-(2,3-dihydro-1H-indol-3-yl)acetate

HRID 2042937Notes

Reaction equation

HRID 2042937 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:2]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:2]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 74706Methyl indole-3-acetate

Product 1

HCID 11816349Methyl 2-(2,3-dihydro-1H-indol-3-yl)acetateYield 77.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of indole 74 (10.9 g, 57.4 mmol) in trifluoroacetic acid (200 mL) was added triethylsilane (20 mL, 121 mmol) at room temperature. The mixture was stirred at 60° C. for 3 h, cooled to room temperature and concentrated in vacuo to remove solvent. The residue was diluted with EtOAc and washed with aq. saturated Cs2CO3 solution. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 75 (8.5 g, 77%). MH+192.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove solvent
  4. additionThe residue was diluted with EtOAc
  5. washwashed with aq. saturated Cs2CO3 solution
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-e52b94198ff8468e8b8eb21896419c3c
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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