Methanol → 3,5-Dimethyl-2-hydroxymethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine

HRID 622158Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12].S(OC)([O:22][CH3:23])(=O)=O.CO.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O>[CH3:1][C:2]1[C:3]([CH2:23][OH:22])=[N:4][CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3,5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide (2.5 g) and dimethyl sulfate (1 ml) was heated at 120° C. for 30 minutes and methanol (12.5 ml) was added, after which a solution of ammonium persulfate (4.3 g) in water (20 ml)-methanol (10 ml) was added dropwise at 80° C. over a period of 30 minutes and the mixture was stirred for 30 minutes. After concentration, ice was added and the mixture was neutralized with sodium carbonate, and then was extracted with chloroform. After drying the extract over sodium sulfate, the solvent was evaporated to give 2.2 g of 3,5-dimethyl-2-hydroxymethyl-4-(2,2,3,3,3pentafluoropropoxy)pyridine as oil.

Workup

concentrationAfter concentration, ice
additionwas added
extractionwas extracted with chloroform
customAfter drying the
extractionextract over sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-2470191b9cc84d31a7bb1d8528010a67
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04769456

Reaction notes

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