Acetaldehyde → 1-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanol

HRID 1786686Notes

Reaction equation

CC1(C)CCCC(C)(C)N1.C([Li])CCC.[CH3:16][O:17][C:18]1[N:19]=[N:20][C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:22][CH:23]=1.[CH:30](=[O:32])[CH3:31]>C1COCC1>[CH3:16][O:17][C:18]1[N:19]=[N:20][C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:22][C:23]=1[CH:30]([OH:32])[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.93 g 2,2,6,6-tetramethylpiperidine in 30 ml THF is added 4.13 ml (15% solution in toluene) n-butyllithium at −30° C. After being stirred at 0° C. for 30 min, the reaction mixture is cooled to −78° C. and a solution of 1.12 g 3-methoxy-6-pyridin-4-yl-pyridazine in 30 ml THF is added and stirred at −78° C. for 30 min. At this temperature, 3.17 g acetaldehyde are added and stirred for another 2 h. The reaction is quenched by the addition of 24 ml MeOH/THF 1:1 and warmed to ambient temperature. Then, 30 ml saturated aq. NaHCO3 are added and extracted with CH2Cl2. The combined organic layers are washed with water, dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (ethyl acetate 100%) to give 0.91 g (66%) of the desired product as a beige solid.

Workup

temperaturethe reaction mixture is cooled to −78° C.
stirringstirred at −78° C. for 30 min
stirringstirred for another 2 h
customThe reaction is quenched by the addition of 24 ml MeOH/THF 1:1
temperaturewarmed to ambient temperature
additionThen, 30 ml saturated aq. NaHCO3 are added
extractionextracted with CH2Cl2
washThe combined organic layers are washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue is purified by flash chromatography (ethyl acetate 100%)

Sources & evidence

ORD record: ord-ef0d5160087c40a19b5856f0bc9e8161
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507734B2

Reaction notes

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