反応 #51861

反応方程式

allyl bromide

lithium bis(trimethylsilyl)amide

[4,5-dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester

ammonium chloride

→

title compound

収率 99.4%

2-[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-pent-4-enoic acid benzyl ester

収率 99.4%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度The mixture was warmed to 0° C. in an ice bath for 30 minutes
2. 2
   workup.DISSOLUTIONto dissolve all solids
3. 3
   温度cooled again to −78° C. in an dry ice/acetone bath
4. 4
   温度the solution warmed to ambient temperature over 2 hours
5. 5
   抽出extracted with ethyl acetate (3×40 cm3)
6. 6
   洗浄The combined ethyl acetate extracts were washed with brine solution (30 cm3)
7. 7
   乾燥dried over sodium sulfate, vacuum
8. 8
   ろ過filtered
9. 9
   その他the filtrate volatile fractions removed in vacuo

実験手順

To a stirred mixture of [4,5-dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester (3.00 g, 6.89 mmol) in anhydrous tetrahydrofuran (50 cm3) under an atmosphere of dry nitrogen cooled to −78° C. in an dry ice/acetone bath was added a 1 M solution of lithium bis(trimethylsilyl)amide (7.60 cm3, 7.60 mmol) in tetrahydrofuran dropwise over 5 minutes. The mixture was warmed to 0° C. in an ice bath for 30 minutes to dissolve all solids and cooled again to −78° C. in an dry ice/acetone bath. Neat allyl bromide (0.720 cm3, 8.27 mmol) was added at −78° C. over 5 minutes and the solution warmed to ambient temperature over 2 hours. Saturated ammonium chloride solution (30 cm3) was added and extracted with ethyl acetate (3×40 cm3). The combined ethyl acetate extracts were washed with brine solution (30 cm3), dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford the title compound as a golden oil (3.25 g, 99.4%) with a positive ion ESI (M+H)+476.3.

出典