Benzyl Alcohol → 1-Benzyl-7-benzyloxy-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734529Notes

Reaction equation

HRID 1734529 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:15]([N:22]1[C:26]2=[C:27](Cl)[N:28]=[N:29][CH:30]=[C:25]2[CH:24]=[C:23]1[CH3:32])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCC1=O>[CH2:15]([N:22]1[C:26]2=[C:27]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:28]=[N:29][CH:30]=[C:25]2[CH:24]=[C:23]1[CH3:32])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 194377481-Benzyl-7-chloro-2-methylpyrrolo[2,3-d]pyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 194377401-Benzyl-7-benzyloxy-2-methylpyrrolo[2,3-d]pyridazineYield 68%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

650 mg (6 mmol) of benzyl alcohol, 10 ml of N-methylpyrrolidone, 1.1 g (10 mmol) of potassium tert-butoxide, 50 mg (0.2 retool) of [18]crown-6 and 500 mg (1.94 retool) of 1-benzyl-7-chloro-2-methylpyrrolo[2,3-d]pyridazine are reacted at room temperature for 2 h. Purification: chromatography on silica gel (eluent: toluene/dioxane=2:1) and crystallization from diisopropyl ether. Yield: 68%, m.p.: 124° C.

Workup

  1. customPurification
  2. customchromatography on silica gel (eluent: toluene/dioxane=2:1) and crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-ff2bbf0a58004ffba39a3770036cd0eb
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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