2-Methylthiophene → 2,2-Dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene

To a cold (-78° C.) solution of 2-methylthiophene (1.2 g, 12.2 mmol) in THF (8 mL) was added n-BuLi in hexane (1.6M, 8.5 mL). The mixture was warmed to ambient temperature over 30 minutes. with stirring. The mixture was recooled to -78° C. and a solution of 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 1.4 g, 5.2 mmol) in THF (10 mL) was added. The mixture was stirred for 16 hours at ambient temperature. Then the reaction mixture was diluted with ether (125 mL), washed with water (10 mL), brine (10 mL) dried and the solvent was removed by evaporation. The product was seperated by column chromatography and was dissolved in dichloromethane (5 mL). To this solution p-TSA (5 mg) was added and the mixture was stirred at ambient temperature for 5 min. The reaction was quenched with 10% NaHCO3 (3 mL), washed with brine (5 mL), dried and the solvent was removed by distillation. The residual crude material was purified by column chromatography to obtain the title compound as a pale yellow oil.

1. customwas recooled to -78° C.
2. stirringThe mixture was stirred for 16 hours at ambient temperature
3. washwashed with water (10 mL), brine (10 mL)
4. customdried
5. customthe solvent was removed by evaporation
6. customThe product was seperated by column chromatography
7. dissolutionwas dissolved in dichloromethane (5 mL)
8. additionTo this solution p-TSA (5 mg) was added
9. stirringthe mixture was stirred at ambient temperature for 5 min
10. customThe reaction was quenched with 10% NaHCO3 (3 mL)
11. washwashed with brine (5 mL)
12. customdried
13. customthe solvent was removed by distillation
14. customThe residual crude material was purified by column chromatography

ORDレコード

ord-4ced6f59ef644dca80ccd38e6f9bbbd4

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05728846