Acetyl chloride → HCID 66670262, compound

HRID 1514652Notes

Reaction equation

HRID 1514652 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]=1)(C)(C)[CH3:2].C(Cl)(=[O:27])C.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.ClCCl>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]=1)(=[O:27])[CH3:2]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 66670203HCID 66670203, compound

Product 1

HCID 66670262HCID 66670262, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Bioorganic & Medicinal Chem. Lett., 14 (2004), 1295-1298, was used as a reference. A 1.00 g portion of ethyl 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate was dissolved in 15 ml of toluene, 0.26 ml of acetyl chloride was added thereto, and 3.6 ml of tin(IV) chloride (a 1 M dichloromethane solution) was added dropwise thereto at 0° C., followed by stirring at room temperature for 6 hours. After adjusting to pH 12 by adding 25 ml of a 1 M sodium hydroxide aqueous solution at 0° C., extraction was carried out with ethyl acetate, followed by washing with saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:7-1:5) to obtain 668 mg of ethyl 5-acetyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate as a beige solid.

Workup

  1. customat 0° C.
  2. extractionextraction
  3. washby washing with saturated brine
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:7-1:5)

Sources & evidence

ORD record
ord-b435ecac0bbe47b5a0f369c00353389c
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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