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

HRID 718554

反応式

HRID 718554 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6131910f8b824feba0b27f5c68ea8b00
出典データセット
uspto-grants-2015_11
特許番号
US09193935B2

関連ノート

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