Sodium Iodide → HCID 87644421, compound

HRID 475556Notes

Reaction equation

[I-].[Na+].[C:3](=[O:6])(O)[O-].[Na+].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:24]2[O:25][CH:26]=[C:27](CCl)[N:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CS(C)=O.[Cl-].[Na+].O>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:24]2[O:25][CH:26]=[C:27]([CH:3]=[O:6])[N:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A 6.81 g quantity of sodium iodide and 5.09 g of sodium bicarbonate were added to a suspension of 10 g of 2-(3-benzyloxy-4-methoxyphenyl)-4-chloromethyloxazole obtained in Reference Example 5 in 60 ml of dimethylsulfoxide. The mixture was heated at 120° C. with stirring for 30 minutes. After the reaction mixture was allowed to cool, saturated brine was added and extraction with ethyl acetate was performed. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give 2.98 g of yellow oily 2-(3-benzyloxy-4-methoxyphenyl)oxazole-4-carbaldehyde.

Workup

temperatureto cool
extractionextraction with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was then distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-8ecdc94792dd4874807ea3e5be72dbb4
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637559B2

Reaction notes

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