Water → HCID 67136311, compound

HRID 230888

Reaction equation

HRID 230888 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([CH:20]=O)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CS(C)=O.[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13](/[CH:20]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 70158464-(benzyloxy)-1H-indole-3-carbaldehyde

Product 1

HCID 67136311HCID 67136311, compoundYield 197.7%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium hydride (60%, 48 mg) in dimethyl sulfoxide (3 mL) was added benzyltriphenylphosphonium chloride (0.47 g), and the mixture was stirred at 65° C. for 1 hour. The reaction mixture was cooled in ice. To the mixture was added 4-benzyloxy-3-formylindole (0.25 g), and the mixture was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature. To the mixture was added water, and the mixture was extracted with ethyl acetate (three times). The extract was washed with water twice, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (0.32 g).

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. stirringthe mixture was stirred at 85° C. for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate (three times)
  5. washThe extract was washed with water twice
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a4df83a8600b4fe4971416a94b0c505e
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Linked notes

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