Diethyl Ether → HCID 22500670, compound

HRID 1815436Notes

Reaction equation

HRID 1815436 reaction equation
[CH2:1]([C:8]1[CH2:9][C:10]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH3:13])[CH2:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=O.C([O-])(O)=O.[Na+].C(OCC)C>CO.O>[CH2:16]([O:15][CH2:14][C:10]1([CH3:13])[CH2:11][N:12]2[C:8](=[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[CH:24]2)[CH2:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 22500672HCID 22500672, compound

Product 1

HCID 22500670HCID 22500670, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

5-Benzyl-3-(benzyloxymethyl)-3-methyl-3,4-dihydro-2H-pyrrole (108 g, 0.368 mol), 2-bromo-1-(4-chlorophenyl)-1-ethanone (100 g, 0.428 mol) and NaHCO3 (34.6 g, 0.42 mol) are dissolved in methanol abs. (950 ml) in a 2 l flask and, adjusted to a temperature of 40° C., stirred for a total of 2 d with exclusion of light. The supernatant methanol phase is poured off from the viscous, green-brown substance at the bottom of the solution formed during the reaction, and the material is taken up with diethyl ether (1 l) and water (800 ml) and partitioned. The water phase is extracted 2 times with ether (600 ml). The collected ether solution is dried over Na2SO4 sicc. and concentrated. Solvent residues are removed in a high vacuum. 124 g of a viscous, swelling residue remain, which consists of the compound sought and which can be employed for. further reactions without further purification. For characterization, the substance is purified by means of column chromatography (Al2O3/hexane-diethyl ether 4:1).

Workup

  1. custom(950 ml) in a 2 l flask and, adjusted to a temperature of 40° C.
  2. customformed during the reaction
  3. custompartitioned
  4. extractionThe water phase is extracted 2 times with ether (600 ml)
  5. dry with materialThe collected ether solution is dried over Na2SO4 sicc
  6. concentrationand concentrated
  7. customSolvent residues are removed in a high vacuum
  8. customfurther reactions without further purification
  9. customFor characterization, the substance is purified by means of column chromatography (Al2O3/hexane-diethyl ether 4:1)

Sources & evidence

ORD record
ord-e095c2bc9634432a905e54d55f0c656b
Source dataset
uspto-grants-2005_04
Patent number
US06878738B1

Reaction notes

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