Acetic Acid → 5-(4-(4-Methoxyphenyl)-3-methylbut-1-enyl)benzo[d][1,3]dioxole

HRID 718554노트

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HRID 718554 반응식
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:10][C:5]=2[O:4][CH2:3]1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([CH3:43])[CH:41]=O)=[CH:35][CH:34]=1.CC(O)=O>C1COCC1>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([CH3:43])[CH:41]=[CH:11][C:9]2[CH:8]=[CH:7][C:6]3[O:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[CH:35][CH:34]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 648132-Methyl-3-(p-methoxyphenyl)propanalHCID 10695955(Benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide

생성물 1

HCID 867027905-(4-(4-Methoxyphenyl)-3-methylbut-1-enyl)benzo[d][1,3]dioxole수율 74.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

Potassium t-pentylat (1.7 M in toluene, 6.5 mL, 11.0 mmol, 1.1 equiv.) was added to a solution of (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide (4.77 g, 10.0 mmol, 1.0 equiv.) in THF (20 mL) at 25° C. After the dark red suspension was stirred at 25° C. for 15 min, 3-(4-methoxyphenyl)-2-methylpropanal (1.78 g, 10.0 mmol, 1.0 equiv.) in THF (10 mL) was added, and the mixture was stirred at 70° C. for 1.5 h. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was extracted with MTBE, the combined organic phases were dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 19:1) to yield 2.20 g (74%) of the title compound as a yellow oil.

후처리

  1. stirringthe mixture was stirred at 70° C. for 1.5 h
  2. extractionthe aqueous layer was extracted with MTBE
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 19:1)

출처 및 근거

ORD 기록
ord-6131910f8b824feba0b27f5c68ea8b00
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193935B2

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