Chlorotrimethylsilane → 9a-butyl-7-methoxymethoxy-4-methyl-3-trimethylsilyloxy-9,9a-dihydro-1H-fluorene

温度

0 °C

A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (163 mg, 0.52 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 0.4M LDA in THF (1.9 mL, 0.78 mmol) was added by syringe. After stirring at 0° C. for 30 minutes, the solution was cooled to −78° C. (dry ice-acetone bath) and treated with chlorotrimethylsilane (0.100 mL, 0.78 mmol). The resulting mixture was allowed to slowly warm to room temperature, then stirred at room temperature overnight. The mixture was diluted with EtOAc (60 mL) and shaken with 5% aqueous NaHCO3 (30 mL). The aqueous phase was separated and extracted with more EtOAc (30 mL). The combined organics were washed with saturated brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil (204 mg). The 1H NMR of this material showed a 9:1 mixture of 9a-butyl-7-methoxymethoxy-4-methyl-3-trimethylsilyloxy-9,9a-dihydro-1H-fluorene and starting material.

1. additionwas added by syringe
2. temperatureto slowly warm to room temperature
3. stirringstirred at room temperature overnight
4. customThe aqueous phase was separated
5. extractionextracted with more EtOAc (30 mL)
6. washThe combined organics were washed with saturated brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum to an oil (204 mg)
10. additiona 9:1 mixture of 9a-butyl-7-methoxymethoxy-4-methyl-3-trimethylsilyloxy-9,9a-dihydro-1H-fluorene

ORDレコード

ord-1359d29ce9324090968a6c78e5d5d25d

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07087599B2