18-Crown-6 → HCID 54495659, compound

HRID 1107772Notes

Reaction equation

HRID 1107772 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.C1OCCOCCOCCOCCOCCOC1.Cl[C:35]1[N:36]=[N:37][CH:38]=[C:39]2[C:43]([CH3:44])=[C:42]([CH3:45])[N:41]([CH2:46][CH:47]=[CH2:48])[C:40]=12>O1CCCC1>[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][O:13][C:35]2[N:36]=[N:37][CH:38]=[C:39]3[C:43]([CH3:44])=[C:42]([CH3:45])[N:41]([CH:46]=[CH:47][CH3:48])[C:40]=23)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 680224-Fluorobenzylic alcoholHCID 18785586HCID 18785586, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54495659HCID 54495659, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.62 g (0.014 mole) of potassium tert-butoxide was added to a solution of 1.02 g (0.0081 mole) of 4-fluorobenzyl alcohol and 0.12 g (0.00045 mole) of 18-crown-6 in 10 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 25 minutes. A solution of 0.60 g (0.0027 mole) of 7-chloro-1-(2-propenyl)-2,3-dimethylpyrrolo[2,3-d]pyridazine in 5 ml of tetrahydrofuran was added dropwise to the mixture and stirred at room temperature for 10 hours. After completion of the reaction, 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 2:3 mixture of ethyl acetate and hexane as an eluent to give 0.33 g of 7-(4-fluorobenzyloxy)-2,3-dimethyl-1-(1-propenyl)pyrrolo[2,3-d]pyridazine (trans) as a pale yellow powder.

Workup

  1. stirringstirred at room temperature for 10 hours
  2. customAfter completion of the reaction
  3. extractionthe aqueous mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel using
  7. additiona 2:3 mixture of ethyl acetate and hexane as an eluent

Sources & evidence

ORD record
ord-376f085f918241d9989c7cd6e382baba
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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