o-Xylyl bromide → HCID 53729059, compound

HRID 399004Notes

Reaction equation

HRID 399004 reaction equation
CC([O-])(C)C.[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:25][O:26][N:27]=[C:28]([C:33]1[NH:34][CH:35]=[CH:36][CH:37]=1)[C:29]([O:31][CH3:32])=[O:30].[CH3:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41]Br>CCOCC>[CH3:25][O:26][N:27]=[C:28]([C:33]1[N:34]([CH2:38][C:39]2[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=2[CH3:41])[CH:35]=[CH:36][CH:37]=1)[C:29]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 6992o-Xylyl bromideHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 136041256HCID 136041256, compound

Product 1

HCID 53729059HCID 53729059, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

4 g (35.7 mmol) of potassium tert-butylate are added to a solution of 730 mg (2.7 mmol) of 18-crown-6 in 50 ml of ether, after which a solution of 5 g (27.5 mmol) of the pyrrole from Example 18 in 50 ml of ether are added dropwise and stirring is carried out for 30 minutes at room temperature. Thereafter, a solution of 6.6 g (37.5 mmol) of o-methylbenzyl bromide in 25 ml of ether is added and 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 using hexane/ethyl acetate gives 4.1 g (52%) of the product as a yellow oil.

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-690f3ebbc5824ca78a29f4ba211b4594
Source dataset
uspto-grants-1998_10
Patent number
US05817682

Reaction notes

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