Trifluoroacetic acid → 5-(3-Chloropropyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 911723Notes

Reaction equation

HRID 911723 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([CH2:17]C)[CH2:15]C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([CH3:17])[CH3:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 673821685-(3-Chloropropyl)-3,3-diethyl-1,3-dihydro-indol-2-one

Product 1

HCID 576560325-(3-Chloropropyl)-3,3-dimethyl-1,3-dihydro-indol-2-oneYield 73%

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, add 5-(3-chloropropyl)-3,3-diethyl-1,3-dihydro-indol-2-one (3.08 g, 12.24 mmol) to trifluoroacetic acid (9.4 mL, 122.4 mmol). Cool the resulting suspension to 0° C. and then add triethylsilane (4.5 mL, 28.2 mmol) dropwise over 2 min. Heat at 45° C. for 30 min then stir at ambient temperature overnight. Pour the reaction mixture onto ice/water (100 mL) and extract with EtOAc (2×100 mL). Dry the combined extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 4:1 gradient), to give the title compound as a yellow-orange solid (2.12 g, 73%).

Workup

  1. temperatureHeat at 45° C. for 30 min
  2. additionPour the reaction mixture onto ice/water (100 mL)
  3. extractionextract with EtOAc (2×100 mL)
  4. dry with materialDry the combined extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 4:1 gradient)

Sources & evidence

ORD record
ord-96d62794dbed47a8bfd16b38b1a942a6
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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