Methanol → {5-[Bis(methyloxy)methyl]-3-bromo-2-pyridinyl}methanol

HRID 1881730Notes

Reaction equation

FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH3:14][O:15][CH:16]([O:26][CH3:27])[C:17]1[CH:18]=[C:19]([Br:25])[C:20]([CH3:24])=[N+:21]([O-])[CH:22]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C(Cl)Cl>[CH3:14][O:15][CH:16]([O:26][CH3:27])[C:17]1[CH:18]=[C:19]([Br:25])[C:20]([CH2:24][OH:4])=[N:21][CH:22]=1

Participants

Conditions

Temperature: 77 °C

Procedure

Trifluoroacetic anhydride (0.191 mL, 1.353 mmol) was added to a solution of 5-[bis(methyloxy)methyl]-3-bromo-2-methylpyridine 1-oxide (118.2 mg, 0.451 mmol) in EtOAc (3 mL) at 0° C. and the mixture was heated at 77° C. in a sealed tube for 6 h and at room temperature overnight. Methanol (0.262 mL, 6.47 mmol) was added and the mixture was stirred at room temperature, and after stirring for 20 min, DCM and 10% Na2CO3 solution were added. Extraction, drying (Na2SO4), and filtration afforded {5-[bis(methyloxy)methyl]-3-bromo-2-pyridinyl}methanol (98 mg, 83%) as a brown oil pure enough to be used in the next step.

Workup

stirringafter stirring for 20 min
extractionExtraction
customdrying
filtration(Na2SO4), and filtration

Sources & evidence

ORD record: ord-bebcfc538b6e476cba67bda68d7b5966
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318940B2

Reaction notes

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