Water → 4,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

HRID 77640

Reaktionsgleichung

Reaktionsgleichung von HRID 77640
[C:1]1([CH:7]=[CH:8][C:9](=[O:21])[CH2:10][C:11](=[O:20])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:25]([C:10]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:11](=[O:20])[CH:12]=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:9](=[O:21])[CH:8]=[CH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 390472Dicinnamoylmethane

Produkt 1

HCID 695017744,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dioneAusbeute 121,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,7-Diphenyl-1,6-heptadiene-3,5-dione (3b, 0.25 g, 0.9 mmol) was stirred in dichloromethane (4 ml) for 5 min at room temperature. A solution of sodium hydroxide (80.0 mg, 2.0 mmol), tetrabutylammonium chloride (0.29 g, 1.0 mmol) and water (2 ml) was added and the mixture stirred for 10 min at room temperature. Benzyl bromide (10, 0.22 ml, 1.8 mmol) was added and the mixture stirred for 1 hr at 40° C. The resulting mixture was cooled to room temperature, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give a solid. The solid was recrystallized from methanol to give 0.25 g (61%) of a white solid: mp 182-183° C. [expected mp 181° C.]; 1H NMR: δ 3.39 (s, 4H), 6.70 (d, 2H, J=15.5 Hz), 7.09-7.44 (m, 20H), 7.73 (d, 2H, J=15.5 Hz); 13C NMR: δ 37.7, 70.3, 123.1, 126.7, 128.1, 128.6, 128.8, 130.3, 130.7, 134.2, 136.3, 142.7, 196.8.

Aufarbeitung

  1. stirringthe mixture stirred for 1 hr at 40° C
  2. temperatureThe resulting mixture was cooled to room temperature
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  9. customto give a solid
  10. customThe solid was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-8a38490a28ae40eab48e52fdb789b460
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

Verknüpfte Notizen

Wird geladen…