Water → HCID 19785052, compound

HRID 256558Notes

Reaction equation

HRID 256558 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[NH:12][C:11]([C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C.C(OCC)C.CCCCCC>[CH2:19]([N:12]1[C:8]([CH3:7])=[CH:9][CH:10]=[C:11]1[C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 23665647Potassium tert-butoxideHCID 54232070HCID 54232070, compound

Product 1

HCID 19785052HCID 19785052, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of potassium tert-butoxide (1.34 g, 12 mmol) in DMF (30 ml) was added dropwise a solution of methyl (5-methylpyrrol-2-yl)oxoacetate (2.0 g, 12 mmol) in DMF (5 ml). The reaction mixture was stirred for 2 hours, cooled to 0° C., and then treated dropwise with a solution of benzyl chloride (1.4 ml, 12 mmol) in DMF (5 ml). The mixture was stirred for 6 hours, poured into water (150 ml) and then extracted with ether (2×100 ml). The organic layers were washed with brine (2×50 ml), dried and then evaporated under reduced pressure to give an orange oil. Chromatography (eluent diethyl ether-hexane 1:1) gave methyl (1-benzyl-5-methylpyrrol-2-yl)oxoacetate (2.0 g) as a yellow oil, 1H nmr: delta 2.22 (3H,s), 3.87 (3H,s), 5.65 (2H,s), 6.1 (1H,d), 7.9 (2H,d), 7.2-7.4 (4H,m) ppm.

Workup

  1. stirringThe mixture was stirred for 6 hours
  2. extractionextracted with ether (2×100 ml)
  3. washThe organic layers were washed with brine (2×50 ml)
  4. customdried
  5. customevaporated under reduced pressure
  6. customto give an orange oil

Sources & evidence

ORD record
ord-77a0a8a23f4d49a99c3da042ec958095
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Reaction notes

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