Chlorotrimethylsilane → HCID 18419719、化合物

温度

-40 °C

Vinylmagnesium bromide (77 ml, 1M THF) was added to a slurry of copper (I) iodide (7.37 g) in tetrahydrofuran (80 ml) at −78° C. under a nitrogen atmosphere. This mixture was stirred at −40° C. for 30 minutes, then recooled to −78° C. A solution of 3-phenyl-5,6-dihydro-2-pyrone (J. Org. Chem. 1967, 32, 2354) (4.6 g) and chlorotrimethylsilane (3.28 ml) in THF (80 ml) was added to the stirred mixture. Thin layer chromatography showed all starting material had reacted. The mixture was quenched with ammonium chloride (saturated aqueous solution) at −78° C. and the resulting mixture was allowed to come to room temperature and was stirred for 2 hours until the aqueous layer became dark blue. The mixture was filtered through Celite™ to remove any insoluble inorganics and the solution was extracted with ethyl acetate (3×100 ml). The pooled organic extracts were washed with brine, dried (MgSO4) and concentrated to give a yellow oil. This was purified on silica using 30-40% ether in hexane as eluant to afford the title compound (4.9 g, crystallised on standing) as a mixture of cis and trans isomers (2:1). Recrystallisation of this mixture from ether-hexane afforded the pure cis isomer as white prisms.

1. customrecooled to −78° C
2. customhad reacted
3. customThe mixture was quenched with ammonium chloride (saturated aqueous solution) at −78° C.
4. customto come to room temperature
5. stirringwas stirred for 2 hours until the aqueous layer
6. filtrationThe mixture was filtered through Celite™
7. customto remove any insoluble inorganics
8. extractionthe solution was extracted with ethyl acetate (3×100 ml)
9. washThe pooled organic extracts were washed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated
12. customto give a yellow oil
13. customThis was purified on silica using 30-40% ether in hexane as eluant

ORDレコード

ord-7b1138bb8ff141f199e993a143c92237

出典データセット

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06458830B1