3,5-Dimethoxybenzyl Bromide → 3-(3,5-Dimethoxyphenyl)-1-propene

HRID 1750045

반응식

HRID 1750045 반응식
[CH:1]([Mg]Br)=[CH2:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10]Br>C1COCC1.[Cu]I>[CH2:10]([C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=1)[CH:1]=[CH2:2]

참가 물질

5

반응물 2

HCID 12744903,5-Dimethoxybenzyl BromideHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 5248743-(3,5-Dimethoxyphenyl)-1-propene수율 100%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of 308 mg (1.62 mmol, 25 mol %) of copper (I) iodide in 30 mL of THF was added dropwise vinylmagnesium bromide as a 1 M solution in THF at −50° C. After stirring for 10 min, a solution of 1.5 g (6.49 mmol) of 3,5-dimethoxybenzyl bromide in 8 mL of THF was added, and the resulting solution was stirred at −30° C. for 1 h and then was warmed to room temperature. The reaction mixture was quenched by the slow addition of 20 mL of water. After stirring for 5 min, the layers were separated and the aqueous layer was extracted twice with 20-mL portions of ethyl acetate. The combined organic fractions were dried (Na2SO4), filtered through a plug of silica gel (eluted with ethyl acetate) and concentrated in vacuo to afford 1.2 g (100%) of product as a yellow oil.

후처리

  1. stirringthe resulting solution was stirred at −30° C. for 1 h
  2. customThe reaction mixture was quenched by the slow addition of 20 mL of water
  3. stirringAfter stirring for 5 min
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted twice with 20-mL portions of ethyl acetate
  6. dry with materialThe combined organic fractions were dried (Na2SO4)
  7. filtrationfiltered through a plug of silica gel (eluted with ethyl acetate)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a6d2ac31885a416292c6aaa5e7957f88
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156836B2

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