Benzaldehyde → 4-Benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

HRID 77639

Reaktionsgleichung

Reaktionsgleichung von HRID 77639
[CH2:1]([CH:8]([C:12](=[O:14])[CH3:13])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(OCCCC)(OCCCC)O[CH2:25][CH2:26][CH2:27]C.[CH2:39](N)[CH2:40][CH2:41][CH3:42].Cl>C(OCC)(=O)C>[CH2:1]([CH:8]([C:9](=[O:11])[CH:10]=[CH:42][C:41]1[CH:27]=[CH:26][CH:25]=[CH:39][CH:40]=1)[C:12](=[O:14])[CH:13]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8007ButylamineHCID 12712Tributyl borateHCID 977572,4-Pentanedione, 3-benzyl-

Produkt 1

HCID 695017244-Benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dioneAusbeute 313,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Boric anhydride (0.49 g, 7.0 mmol) was combined with 3-benzyl-2,4-pentanedione (8, 1.90 g, 10.0 mmol) and stirred for 48 hr at room temperature under a nitrogen atmosphere. A solution of dry ethyl acetate (10 ml), benzaldehyde (1b, 2.05 ml, 20.2 mmol) and tributyl borate (11.0 ml, 40.5 mmol) was added and the mixture stirred for 15 min at room temperature. Butylamine (0.20 ml, 2.0 mmol) was added dropwise over 30 min and stirring was continued for 18 hr at room temperature. Hydrochloric acid (15 ml, 0.4 N) was warmed to 60° C., added to the mixture and stirring was continued for 1 hr. The resulting mixture was filtered to afford a solid. The crude solid was triturated with methanol to give 2.30 g (63%) of a yellow solid: mp 162-164° C. [expected mp 156-158° C.]; 1H NMR: δ 3.99 (s, 2H), 6.99 (d, 2H, J=15.6 Hz), 7.34 (m, 15H), 7.77 (d, 2H, J=15.2 Hz); 13C NMR: δ 31.8, 109.3, 120.8, 126.5, 127.8, 128.1, 128.8, 130.0, 135.3, 140.5, 141.9, 183.6.

Aufarbeitung

  1. stirringthe mixture stirred for 15 min at room temperature
  2. stirringstirring
  3. waitwas continued for 18 hr at room temperature
  4. additionadded to the mixture
  5. stirringstirring
  6. waitwas continued for 1 hr
  7. filtrationThe resulting mixture was filtered
  8. customto afford a solid
  9. customThe crude solid was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-2e9fa605a42840959f88d791f2c4ede4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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