Diisobutylaluminumhydride → HCID 86677031, compound

HRID 927113Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](OCC)=[O:24])[N:12]=[N:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[O:24])[N:12]=[N:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

Ethyl 5,6-bis(benzyloxy)pyridazine-3-carboxylate (Intermediate 62; 3.8 g, 10.43 mmol) was dissolved in THF (95 ml) and cooled to 0-5° C. under nitrogen atmosphere. A solution of di-isobutyl-aluminium hydride in THF (1 M, 21 ml, 20.8 mmol) was added at 0-5° C. and reaction mixture was stirred at room temperature for 2 hours. Upon completion the reaction was quenched by the addition of ethyl acetate and then saturated aqueous ammonium chloride solution. The resulting mass was filtered and extracted into ethyl acetate (3×50 ml) and the combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica, eluting with dichloromethane) to afford 5,6-bis(benzyloxy)pyridazine-3-carbaldehyde (2.9 g, 87% yield).

Workup

customreaction mixture
customUpon completion the reaction was quenched by the addition of ethyl acetate
filtrationThe resulting mass was filtered
extractionextracted into ethyl acetate (3×50 ml)
washthe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (silica, eluting with dichloromethane)

Sources & evidence

ORD record: ord-7100a2da2564437480eb33215891c9c9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290456B2

Reaction notes

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