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

HRID 252311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252311
[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

Komponenten

7

Edukt 3

HCID 6340IodoethaneHCID 10018825HCID 10018825, VerbindungHCID 10468248(E)-2-ethyl-1,3-diMethoxy-5-styrylbenzene2×

Produkt 2

HCID 5316874Pinosylvin, dimethyl etherAusbeute 30 %HCID 10468248(E)-2-ethyl-1,3-diMethoxy-5-styrylbenzeneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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′).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-742bd6be7a9e4a0483762a78085526d8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868047B2

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