Water → HCID 86584359, compound

HRID 1368064Notes

Reaction equation

HRID 1368064 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[NH:17][CH:18]=[CH:19][CH:20]=2)=O)=[CH:10][CH:9]=1.ClCC[O:24]C.[OH2:26]>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][N:17]([O:26][CH2:1][CH2:2][CH3:3])[C:16]=2[CH:20]=[O:24])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123162-Chloroethyl methyl ether3×HCID 640241(4-chlorophenyl)(1H-pyrrol-2-yl)methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86584359HCID 86584359, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4.8 mL (0.062 mole) of potassium t-butoxide 1.OM in THF added dropwise to 10 g (0.048 mole) of (4-chlorophenyl)-1H-pyrrol-2-ylmethanone in 60 mL of THF. After stirring for 20 minutes, a solution of 5.6 mL (0.062 mole) of chloroethylmethyl ether in 40 mL of THF was added dropwise. The reaction mixture was refluxed for 72 h after which 5 mL of chloroethylmethyl ether was added and refluxing continued overnight. Another 5 mL of chloroethylmethyl ether was added with an additional 24 h of refluxing. The reaction was poured into water and extracted with Et2O. The organics were washed with water, brine and dried (MgSO4). The solvent was evaporated in vacuo to give 10.5 g (83%) of [(4-chlorophenyl)-1-ethylmethoxy-1H-pyrrol-2-yl]methanone. CIMS m/z 264 (MH+). 1H NMR (300 MHz, CDCl3) δ 7.75 (d, 2H); 7.45 (d, 2H); 7.1 (Ar, 1H); 6.75 (Ar, 1H) 6.2 (Ar, 1H) 4.6 (t, 2H); 3.75 (t, 2H); 3.3 (s, 3H).

Workup

  1. additionwas added
  2. temperaturerefluxing continued overnight
  3. temperatureof refluxing
  4. extractionextracted with Et2O
  5. washThe organics were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0390591295ec430e87e304ffece31404
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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