Water → HCID 67792972, compound

HRID 486063Notes

Reaction equation

HRID 486063 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:20]([O:22][C:23](=[O:27])[CH2:24][CH2:25]Cl)[CH3:21].O>CN(C)C=O>[CH2:20]([O:22][C:23]([CH:24]([C:15]1[NH:16][C:17]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:10][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[CH:19][CH:18]=2)[CH3:25])=[O:27])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 69341Ethyl 3-chloropropionate

Product 1

HCID 67792972HCID 67792972, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 60% sodium hydride (15 g) in dimethylformamide (30 ml) was added a N,N-dimethylformamide solution of 5-benzyloxyindole (5.0 g) at 0° C. After 15 minutes a solution of ethyl-3-chloropropionate (3.1 ml) in N,N-dimethylformamide was added dropwise and the reaction mixture stirred for a further 5 hours at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 15%-ethyl acetate in n-hexanes to yield the title product (6.81 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 15%-ethyl acetate in n-hexanes

Sources & evidence

ORD record
ord-6460ef50c7654d0bb18135d33e8725a3
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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