Iodoethane → (E)-2-ethyl-1,3-diMethoxy-5-styrylbenzene

HRID 252311ノート

反応式

HRID 252311 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[CH2:9][CH3:10].[CH3:21][O:22][C:23]1[CH:24]=[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:26]=[C:27]([O:30][CH3:31])[C:28]=1Br.C(I)C>C1COCC1.O>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[CH2:9][CH3:10].[CH3:31][O:30][C:27]1[CH:26]=[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=1

参加物

7

反応物 3

HCID 6340IodoethaneHCID 10018825HCID 10018825、化合物HCID 10468248(E)-2-ethyl-1,3-diMethoxy-5-styrylbenzene2 回

生成物 2

HCID 5316874Pinosylvin, dimethyl ether収率 30%HCID 10468248(E)-2-ethyl-1,3-diMethoxy-5-styrylbenzene収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

3,5-Dimethoxy-4-ethyl-trans-stilbene (compound 15A-a in Scheme 5): t-butyl Li (1.1 mL, 1M in THF) was added at −78° C. to a THF solution (10 mL) containing 3,5-dimethoxy-4-bromo-trans-stilbene (0.53 g). After addition, the solution was slowly heated to reflux for 30 min and then cooled down to −78° C. Ethyl iodide (1.2 eq, 0.265 mL) was added to the solution at −78° C. After reaction finished, water (10 mL) was added dropwise to the mixture, THF was evaporated under reduced pressure. The mixture was extracted with CH2Cl2 (5 mL×3), the combined organic layer was dried over anhydrous magnesium sulfate, and remove under reduced pressure. The product mixture was purified by column chromatography (ether/pet ether=1:8) and gave 3,5-dimethoxy-4-ethyl-trans-stilbene (15A-a) (70%) and 3,5-dimethoxy-trans-stilbene (30%) due to the moisture. Mp: 70-73° C. NMR (400 MHz, CDCl3): δ 1.12 (t, 6H, J=7.2 Hz, CH3), 2.70 (q, 2H, —CH2—), 3.91 (s, 6H, OCH3), 6.74 (s, 2H, H-2, 6), 7.07 (s, 2H), 7.26 (m, 1H, H-4′), 7.36 (m, 2H, H-3′, 5′), 7.52 (m, 2H, H-2′, 6′).

後処理

  1. additionAfter addition
  2. temperaturethe solution was slowly heated
  3. temperatureto reflux for 30 min
  4. customAfter reaction
  5. customwas evaporated under reduced pressure
  6. extractionThe mixture was extracted with CH2Cl2 (5 mL×3)
  7. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  8. customremove under reduced pressure
  9. customThe product mixture was purified by column chromatography (ether/pet ether=1:8)

出典と根拠

ORDレコード
ord-742bd6be7a9e4a0483762a78085526d8
出典データセット
uspto-grants-2011_01
特許番号
US07868047B2

反応ノート

読み込み中…