Benzyl Bromide → HCID 18973498, compound

HRID 2394452Notes

Reaction equation

HRID 2394452 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:15]=[O:16])[C:9]=2[CH:8]=[CH:7]1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:23]([O:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:15]=[O:16])[C:9]=2[CH:8]=[CH:7]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18973329HCID 18973329, compound

Product 1

HCID 18973498HCID 18973498, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

There was suspended 26.4 mg of 60% sodium hydride in 5 ml of dimethylformamide, followed by addition of a solution of 1-(2-hydroxy-2-phenylethyl)indole-4-carbaldehyde (160 mg) in dimethylformamide (2 ml) with ice-cooling. After stirring at room temperature for 15 minutes, the mixture was ice-cooled, then a solution of benzyl bromide (115.2 mg) in dimethylformamide (2 ml) was added thereto and stirred at room temperature for 3 hours. The reaction system was poured into 50 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (50 ml×2). The resulting organic phase was washed with, in order, a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 170 mg of 1-(2-benzyloxy-2-phenylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 80%.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringstirred at room temperature for 3 hours
  4. extractionextracted with ethyl acetate (50 ml×2)
  5. washThe resulting organic phase was washed with, in order
  6. dry with materiala 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate
  7. customthe solvent was removed through evaporation under reduced pressure
  8. customto give a crude product
  9. customThe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1222c1e9b10c4f59888c121612ff5341
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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