Chloroform → HCID 54381456, compound

HRID 224661Notes

Reaction equation

HRID 224661 reaction equation
[C:1]([C:9]1[CH:13]=[C:12]([CH3:14])[N:11]([CH:15]([CH3:18])[CH2:16][OH:17])[C:10]=1[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl>C(Cl)Cl>[C:20]([O:17][CH2:16][CH:15]([N:11]1[C:12]([CH3:14])=[CH:13][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]1[CH3:19])[CH3:18])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 194460[1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

Product 1

HCID 54381456HCID 54381456, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride were dissolved 140 mg (0.54 mmole) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl) 2-methylethanol and 383 mg (2.75 mmoles) of benzoyl chloride. Triethylamine (1 ml) was added to the solution, and the mixture was stirred at room temperature for 20 hours. Chloroform was added to the reaction mixture. The mixture was washed with dilute hydrochloric acid and then with an aqueous solution of sodium hydrogen carbonate, and the resulting extract was dried over anhydrous magnesium sulfate, and concentrated to afford 860 mg of a crude product. The product was chromatographed on a column of silica gel using cyclohexane/ethyl acetate (3/1) as an eluent to afford compound (314) (150 mg, 0.42 mmole, 77.8%).

Workup

  1. washThe mixture was washed with dilute hydrochloric acid
  2. extractionwith an aqueous solution of sodium hydrogen carbonate, and the resulting extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto afford 860 mg of a crude product
  6. customThe product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-a75d5cd966e0414ca132433b2fb5370b
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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