Diethyl Ether → HCID 10489167, compound

HRID 1368062Notes

Reaction equation

HRID 1368062 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[CH:17]=[CH:16][N:15](S(C2C=CC(C)=CC=2)(=O)=O)[CH:14]=1)=[O:12].O1CCOCC1.[OH-].[Na+].CCOCC>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[CH:17]=[CH:16][NH:15][CH:14]=1)=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18519864HCID 18519864, compound

Product 1

HCID 10489167HCID 10489167, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a flask was placed 46 g (0.12 mole) of 3-(2-naphthalenoyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole, 250 mL of 1,4-dioxane and 59.8 mL (0.18 mole) of 3 N NaOH. The reaction mixture was stirred overnight after which Et2O and water were added. The organics were separated off, washed with water, brine and dried (Na2SO4). Evaporation of the solvent in vacuo and crystallization from toluene gave 13.5 g of (51%) 3-(2-naphthalenoyl)-1H-pyrrole. mp134-136° C. CIMS m/z 223 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.35 (Ar, 1H); 7.9 (Ar, 4H); 7.7 (Ar, 1H); 7.5 (Ar, 2H); 7.4 (Ar, 1H); 6.85 (Ar, 1H).

Workup

  1. customInto a flask was placed
  2. additionwere added
  3. customThe organics were separated off
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customin vacuo and crystallization from toluene

Sources & evidence

ORD record
ord-478639df9bdb463aa0c665783da583e0
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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