Hydrochloric Acid → HCID 86658000, compound

HRID 70513Notes

Reaction equation

Cl.[Si:2]([O:19][CH2:20][C:21]1[C:22]([O:32][CH3:33])=[N:23][C:24]([CH:27](OC)[O:28]C)=[CH:25][CH:26]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>O1CCCC1>[Si:2]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[N:23][C:22]=1[O:32][CH3:33])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1 M hydrochloric acid (40 mL) was added to a solution of 3-({[tert-butyl(diphenyl)silyl]oxy}methyl)-6-(dimethoxymethyl)-2-methoxypyridine (5.47 g) in tetrahydrofuran (40 mL), and the mixture was stirred at 60° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1) to give 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-6-methoxypyridine-2-carbaldehyde (3.2 g, 73%) as a colorless oil.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1)

Sources & evidence

ORD record: ord-a132f3480d1e4b5683aa0f7d6f9e6028
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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