tert-Butanol → 2-{1-[3-(tert-Butyldimethylsilyloxy)propyl]-1H-indol-4-yl}acetamide

HRID 751504Notes

Reaction equation

HRID 751504 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[C:16]([CH2:21][C:22]#[N:23])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC([OH:28])(C)C.[OH-].[K+]>C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[C:16]([CH2:21][C:22]([NH2:23])=[O:28])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium Hydroxide2×HCID 17985901{1-[3-(tert-Butyldimethylsilyloxy)propyl]-1H-indol-4-yl}acetonitrile

Product 1

HCID 692694502-{1-[3-(tert-Butyldimethylsilyloxy)propyl]-1H-indol-4-yl}acetamideYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add {1-[3-(tert-Butyldimethylsilyloxy)propyl]-1H-indol-4-yl}acetonitrile (1.9 g, 11.0 mmol) to 2-methyl-2-propanol (20 mL). Heat to reflux under nitrogen and add potassium hydroxide pellets (7.4 g, 132 mmol). Stir and reflux under nitrogen for 30 minutes. Pour solution off of the excess potassium hydroxide and dilute with ethyl acetate. Wash with a 1:1 mixture of aqueous saturated sodium chloride, aqueous saturated sodium hydrogen carbonate. Dry the organic phase over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Rinse the solid with cold diethyl ether and dry under vacuum to obtain 1.62 g (77%) of the title compound as an off-white solid. ESMS (M++1): 347.2.

Workup

  1. temperatureHeat
  2. temperatureto reflux under nitrogen
  3. temperaturereflux under nitrogen for 30 minutes
  4. washWash with a 1:1 mixture of aqueous saturated sodium chloride, aqueous saturated sodium hydrogen carbonate
  5. dry with materialDry the organic phase over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. washRinse the solid with cold diethyl ether
  9. customdry under vacuum

Sources & evidence

ORD record
ord-8c5c32502d4043be8e94db4741c9615a
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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