Water → HCID 9880270, compound

HRID 586616Notes

Reaction equation

HRID 586616 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[F:13][C:14]1[CH:25]=[CH:24][C:17]([CH2:18][C:19]2[CH2:23][CH2:22][CH2:21][N:20]=2)=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+].O>C(OCC)C.C(O)C>[F:13][C:14]1[CH:25]=[CH:24][C:17]([C:18]2[C:3]([C:5]3[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=3)=[CH:2][N:20]3[C:19]=2[CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanoneHCID 139464605-[(4-Fluorophenyl)methyl]-3,4-dihydro-2H-pyrrole

Product 1

HCID 9880270HCID 9880270, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Bromo-1-(4-methylsulphanylphenyl)-1-ethanone (0.83 g, 3.4 mmol), dissolved in diethyl ether (10 ml), is treated with a solution of 2-(4-fluorobenzyl)-1-pyrroline (0.6 g, 3.3 mmol) in ethanol (10 ml) and NaHCO3 (0.6 g, 7 mmol). The mixture is stirred in the dark at RT for 18 h. The reaction is checked by TLC: SiO2/hexane-ether 9:1. The mixture is treated with H2O (10 ml), extracted 2 times with diethyl ether (100 ml) and the combined ether phase is then rewashed with water (30 ml). The organic phase dried over Na2SO4 Sicc. is concentrated in vacuo. The residue which remains is purified by CC on Al2O3/hexane/diethyl ether 1:1. Fractions 1-3 afford 330 mg of orange-red oil.

Workup

  1. extractionextracted 2 times with diethyl ether (100 ml)
  2. dry with materialThe organic phase dried over Na2SO4 Sicc
  3. concentrationis concentrated in vacuo
  4. customThe residue which remains is purified by CC on Al2O3/hexane/diethyl ether 1:1

Sources & evidence

ORD record
ord-0f903e167af14f79a6c3e71a3c4a4129
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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