4-Chlorobenzoyl chloride → HCID 53927902, compound

HRID 845511Notes

Reaction equation

HRID 845511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=[CH:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]2.[H-].[Na+].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>O1CCCC1>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 24758Sodium hydrideHCID 54071276HCID 54071276, compound

Product 1

HCID 53927902HCID 53927902, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 5-(5-methoxyindol-2-yl)-2,4-pentadienoate (0.8 g, 2.9 mmol) in 20 ml of tetrahydrofuran (THF) was added dropwise to a suspension of sodium hydride (0.024 g of a 60% reagent) at 0° C. (ice bath). After addition, the mixture was stirred in the ice bath for 1 hour and a solution of p-chlorobenzoyl chloride (0.54 g) in 10 ml of THF was added; the resulting mixture was filtered to remove the precipitate and the filtrate was washed with brine, dried (magnesium sulfate) and concentrated on rotary evaporator to give a yellow oil. Crystallization of this oily substance from acetone-ether afforded 0.75 g of ethyl 5-(1-p-chlorobenzoyl-5-methoxyindol-2-yl)-2,4-pentadienoate as yellow powders, m.p., 121°-125° C. MS(EI): 40 g(M+), 336 (M+ --CO2Et).

Workup

  1. additionAfter addition
  2. filtrationthe resulting mixture was filtered
  3. customto remove the precipitate
  4. washthe filtrate was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated on rotary evaporator
  7. customto give a yellow oil
  8. customCrystallization of this oily substance from acetone-ether

Sources & evidence

ORD record
ord-09eb2af52c67450885b893086af5f45f
Source dataset
uspto-grants-1988_07
Patent number
US04758586

Reaction notes

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