Sodium hydride → 3,3,7-Trimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one

HRID 1176524Notes

Reaction equation

HRID 1176524 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[H-].[Na+].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl>CN(C)C=O>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[C:3]1=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 151874723,3,7-Trimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 685015123,3,7-Trimethyl-1-(2-trimethylsilanylethoxymethyl)-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The stirred solution of 2.00 g of 3,3,7-trimethyl-1,3-dihydroindol-2-one and 10 ml of N,N-dimethylformamide is cooled to 0° C. and admixed with 0.479 g of sodium hydride dispersion (60%). The mixture is stirred at 0° C. over 1 hour and subsequently admixed with 2.33 ml of 2-(trimethylsilyl)ethoxymethyl chloride. The ice bath is removed and the reaction mixture is stirred further at room temperature over 14 hours. The reaction mixture is poured onto ice-water (100 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed successively with water (2×100 ml) and brine (1×100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.51 (1:3 EtOAc-heptane); Rt=5.93.

Workup

  1. customThe ice bath is removed
  2. stirringthe reaction mixture is stirred further at room temperature over 14 hours
  3. additionThe reaction mixture is poured onto ice-water (100 ml)
  4. extractionextracted with tert-butyl methyl ether (2×100 ml)
  5. washThe organic phases are washed successively with water (2×100 ml) and brine (1×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a057236893684ed4a8e67566d5c226b3
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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