반응 #57615

반응 방정식

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

수율 80.6%

용매

THF

반응 조건

후처리

1. 1
   온도The reaction was cooled in an ice bath
2. 2
   온도The reaction was heated at ˜50° C. for 1 hour
3. 3
   온도cooled to room temperature
4. 4
   추출the resulting mixture was extracted with ethyl acetate
5. 5
   세척The organic layer washed with water and brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1)

실험 절차

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)+.

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