Sodium hydride → HCID 54396318、化合物

温度

0 °C

To a cold (0° C.) suspension of NaH (5.4 g, 60% suspension in mineral oil) in anhydrous ether (180 ml) was added dropwise a mixture of 1-n-butyltosylmethylisocyanide (29 g) and methyl butadienecarboxylate (12.2 ml) in anhydrous ether (180 ml) and dry dimethyl sulfoxide (90 ml) under an inert atmosphere. The reaction mixture was first stirred at 0° C. for 1 hour and then slowly brought to room temperature and the stirring continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and cautiously poured onto aqueous saturated ammonium chloride solution (200 ml). The organic layer was separated, and the aqueous layer was thoroughly extracted with ethyl acetate. The combined ether and ethyl acetate extracts were sequentially washed with saturated ammonium chloride solution in cold water, and then brine, and dried with magnesium sulfate. The solvent was removed under vacuum and the residue purified by column chromatography on silica gel, eluting with 15% ethyl acetate/hexane, to afford methyl 3-[2-(n-butyl)pyrrol-4-yl]acrylate as a yellow oil (15.32 g), a compound of Formula (52), which crystallized on standing to a solid, m.p. 65°-67° C.

1. additionwas added dropwise
2. customslowly brought to room temperature
3. waitthe stirring continued for an additional 6 hours
4. temperatureThe reaction mixture was then cooled to 0° C.
5. customThe organic layer was separated
6. extractionthe aqueous layer was thoroughly extracted with ethyl acetate
7. washThe combined ether and ethyl acetate extracts were sequentially washed with saturated ammonium chloride solution in cold water
8. dry with materialbrine, and dried with magnesium sulfate
9. customThe solvent was removed under vacuum
10. customthe residue purified by column chromatography on silica gel
11. washeluting with 15% ethyl acetate/hexane

ORDレコード

ord-277a43d23ffc47b2bf554caaaf842819

出典データセット

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05380739