反応 #57615

反応方程式

sodium percarbonate

3-methyl-4-vinyl-1-benzofuran-2-carboxylate

3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

borane THF

Water

water

→

ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate

収率 80.6%

溶媒

THF

反応条件

後処理

1. 1
   温度The reaction was cooled in an ice bath
2. 2
   温度The reaction was heated at ˜50° C. for 1 hour
3. 3
   温度cooled to room temperature
4. 4
   抽出the resulting mixture was extracted with ethyl acetate
5. 5
   洗浄The organic layer washed with water and brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1)

実験手順

To a solution of 0.35 g (1.5 mmol) of 3-methyl-4-vinyl-1-benzofuran-2-carboxylate (Example 87, Step 1) in 3 mL of THF, cooled in an ice bath, was added 1 mL (1 mmol) of borane-THF complex (1.0M solution in THF). The reaction was stirred at room temperature for 2 hours. The reaction was cooled in an ice bath and 1.5 mL of water was added. Next 0.61 g of sodium percarbonate was added in one portion. The reaction was heated at ˜50° C. for 1 hour, then cooled to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1) to provide 0.20 g of ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate. Yield 54%. m.p. 88-90° C.; MS 249.1 (M+H)+.

出典