Sodium hydride → 4-(5,9-Dioxaspiro[3.5]non-7-yloxy)-2,3-dimethylpyridine 1-oxide

To a dimethyl formamide (30 ml) solution of the 5,9-dioxaspiro[3.5]nonan-7-ol (1.68 g, 11.7 mmol) obtained in the step (9e), sodium hydride, in oil (587 mg, 13.5 mmol as the content was regarded as 55%) was added at room temperature. The mixture was stirred at room temperature for 50 minutes. After 4-chloro-2,3-dimethylpyridine 1-oxide (1.84 g, 11.7 mmol) was added thereto, the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated and dimethylsulfoxide (30 ml) was added thereto and stirred at 80° C. After 12 hours, sodium hydride, in oil (587 mg, 13.5 mmol as the content was regarded as 55%) was added to the reaction mixture and stirred at 80° C. After one hour, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1) to obtain the title compound (2.00 g, yield: 64.4%) as a light yellow oil.

1. additionwas added at room temperature
2. stirringthe mixture was stirred at 80° C. for 2 hours
3. concentrationThe reaction mixture was concentrated
4. additiondimethylsulfoxide (30 ml) was added
5. stirringstirred at 80° C
6. waitAfter 12 hours
7. additionwas added to the reaction mixture
8. stirringstirred at 80° C
9. waitAfter one hour
10. concentrationthe reaction mixture was concentrated
11. customthe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1)

ORDレコード

ord-6fa38296534a463ba0f81448cef149f3

出典データセット

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07425634B2