Sodium hydride → HCID 67392595, compound

HRID 907366Notes

Reaction equation

C(OP([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)(OCC)=O)C.[H-].[Na+].[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]([CH:32]=O)[CH:23]=1>C1COCC1>[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24](/[CH:32]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)[CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 4-[(diethoxyphosphoryl)methyl]benzoate (0.911 g, 3.18 mmol; see Preparation 4(i) above) in THF (10 mL, dry) under a nitrogen atmosphere was added sodium hydride (0.678 g, 60%, 18.8 mmol). After cooling the reaction mixture to 0° C., quinoline-3-aldehyde (0.500 g, 3.18 mmol) in THF (10 mL, dry) was carefully added dropwise with stirring. The reaction mixture was stirred for 1 h at room temperature and then quenched with water. After neutralisation with dilute HCl, the two layers were separated, the water layer extracted with ethyl acetate and the organic layers were combined, dried (MgSO4), filtered and the solvent removed under reduced pressure to give a white solid. The product was purified by silica gel column chromatography using 25% ethyl acetate/n-hexane (RF=0.50) to give the sub-title compound (0.900 g, 98%), as a white solid, m.p.=92-94° C.

Workup

stirringThe reaction mixture was stirred for 1 h at room temperature
customquenched with water
customAfter neutralisation with dilute HCl, the two layers were separated
extractionthe water layer extracted with ethyl acetate
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent removed under reduced pressure
customto give a white solid
customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-22b697729ae54840935decedb0763587
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012967B2

Reaction notes

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