18-Crown-6 → HCID 18785577, compound

HRID 1107769Notes

Reaction equation

HRID 1107769 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[N:16]=[N:17][CH:18]=[C:19]2[C:23]([CH3:24])=[C:22]([CH3:25])[NH:21][C:20]=12)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1OCCOCCOCCOCCOCCOC1.[Cl:44][C:45]([Cl:49])=[CH:46][CH2:47]Br>O1CCCC1>[CH2:7]([O:14][C:15]1[N:16]=[N:17][CH:18]=[C:19]2[C:23]([CH3:24])=[C:22]([CH3:25])[N:21]([CH2:47][CH:46]=[C:45]([Cl:49])[Cl:44])[C:20]=12)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 126424063-Bromo-1,1-dichloroprop-1-eneHCID 187856837-Benzyloxy-2,3-dimethylpyrrolo[2,3-d]pyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18785577HCID 18785577, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.13 g (0.0011 mole) of potassium tert-butoxide was added to a suspension of 0.29 g (0.0011 mole) of 7-benzyloxy-2,3-dimethylpyrrolo[2,3-d]pyridazine and 0.03 g (0.0001 mole) of 18-crown-6 in 8 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 40 minutes. 0.22 g (0.0011 mole) of 3,3-dichloro-2-propenyl bromide was then added to the mixture and stirred at room temperature for 5 minutes. The reaction mixture was poured into ice-water and the aqueous mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 20:1 mixture of chloroform and methanol as an eluent to give 0.090 g of 7-benzyloxy-1-(3,3-dichloro-2-propenyl)-2,3-dimethylpyrrolo[2,3-d]pyridazine as a yellow powder.

Workup

  1. stirringstirred at room temperature for 5 minutes
  2. extractionthe aqueous mixture was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel using
  6. additiona 20:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-6a342b8c982a45fe9ba85e96c2e2d926
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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