Propanal → HCID 67276554, compound

HRID 1696702Notes

Reaction equation

[Li]CCCC.CCCCCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][N:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:27](=[O:30])[CH2:28][CH3:29].[Cl-].[NH4+]>C1COCC1>[CH2:12]([O:19][C:20]1[N:21]=[CH:22][C:23]([CH:27]([OH:30])[CH2:28][CH3:29])=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a nitrogen atmosphere at −78° C., 2.71 M n-BuLi/hexane solution (18.8 mL) was dropwise added to a THF solution of 2-(benzyloxy)-5-bromopyridine (12.2 g, 46.2 mmol) synthesized according to the method described in a reference (J. Org. Chem., 1995, Vol. 60, p. 1408), and stirred at −78° C. for 1 hour. At −78° C., propionaldehyde (4.3 mL) was dropwise added, and stirred at −78° C. for 30 minutes and then at room temperature for 3 hours. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, then dried with magnesium sulfate and concentrated. This was purified by silica gel column chromatography to obtain the intended compound (7.15 g, 64%) as a yellow oil.

Workup

customsynthesized
stirringstirred at −78° C. for 30 minutes
waitat room temperature for 3 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried with magnesium sulfate
concentrationconcentrated
customThis was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-41473cbaaf3d4bf682df948ff6fbb9ad
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163770B2

Reaction notes

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