Benzyl Bromide → HCID 21843483, compound

HRID 1737842Notes

Reaction equation

HRID 1737842 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].C1OCCOCCOCCOCCOCCOC1.CC([O-])(C)C.[K+].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CCOCC>[CH2:36]([N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 2855718-Crown-6HCID 18370696HCID 18370696, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21843483HCID 21843483, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A suspension of 10 g (65 mmol) of methyl pyrrol-2-ylglyoxylate in 100 ml of ether is added to a solution of 1.7 g (6.5 mol) of 18-crown-6 with 7.3 g (65 mmol) of potassium tert-butylate in 100 ml of ether, stirring is carried out for 30 minutes and 11.1 g (65 mmol) of benzyl bromide in 50 ml of ether are then added dropwise. Stirring is carried out overnight at room temperature, the mixture is poured onto water and extracted with ether and the organic phase is dried and evaporated down. Chromatography over silica gel with hexane/ethyl acetate gives 6.7 g (42%) of the title compound as a reddish brown oi.

Workup

  1. stirringStirring
  2. waitis carried out overnight at room temperature
  3. additionthe mixture is poured onto water
  4. extractionextracted with ether
  5. customthe organic phase is dried
  6. customevaporated down

Sources & evidence

ORD record
ord-a5fc7e18c4e1434588e2fda96d3afa5f
Source dataset
uspto-grants-1999_10
Patent number
US05962489

Reaction notes

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