Methanol → HCID 66658029, compound

HRID 1881727Notes

Reaction equation

HRID 1881727 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[Cl:14][C:15]1[C:16]([CH3:27])=[N+:17]([O-])[CH:18]=[C:19]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:20]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:14][C:15]1[C:16]([CH2:27][OH:4])=[N:17][CH:18]=[C:19]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 666582803-Chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxide

Product 1

HCID 66658029HCID 66658029, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic anhydride (231 μl, 1.635 mmol) was added to a solution of 3-chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxide (225 mg, 1.043 mmol) in DCM (4 ml) at 0° C. and the mixture was stirred at room temperature for 48 h. Full conversion was observed by HPLC. MeOH (0.5 ml, 12.36 mmol) was added and, after stirring for 10 min, DCM and 10% Na2CO3 solution were added. Extraction, drying (MgSO4), and filtration afforded 223.2 mg of crude material. Purification by flash chromatography using Flashmaster II, a 5 g silica gel cartridge, and mixtures of hexane and EtOAc as eluent afforded [3-chloro-5-(1,3-dioxolan-2-yl)-2-pyridinyl]methanol (142.7 mg, 63%) as a yellow oil.

Workup

  1. stirringafter stirring for 10 min
  2. extractionExtraction
  3. customdrying
  4. filtration(MgSO4), and filtration
  5. customafforded 223.2 mg of crude material
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-bdf56b0d52bb4883b98d9fb354f1f982
Source dataset
uspto-grants-2012_11
Patent number
US08318940B2

Reaction notes

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