Water → Bis-(3-benzyloxy-4-methoxyphenyl)methanol

HRID 1685642

Reaktionsgleichung

Reaktionsgleichung von HRID 1685642
[Li]CCCC.[CH2:6]([O:13][C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:23]([O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH:34]=[O:35])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1COCC1>[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([CH:34]([C:33]2[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:31]([O:30][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:32]=2)[OH:35])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 149128522-(Benzyloxy)-4-bromo-1-methoxybenzeneHCID 178418339Butyllithium

Produkt 1

HCID 58734013Bis-(3-benzyloxy-4-methoxyphenyl)methanolAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

n-BuLi (1.6 M, 5.2 mL) was added to a solution of 2-benzyloxy-4-bromo-1-methoxybenzene (2.10 g, 7.2 mmol) in THF (28 mL) at −78° C. and the resulting yellow solution was stirred at this temperature for 1 h. A solution of 3-benzyloxy-4-methoxybenzaldehyde (1.74 g, 7.2 mmol) in THF (16 mL) was added dropwise at −78° C. and the reaction mixture was stirred at this temperature for 1.5 h and then at room temperature for 2 h. Water (100 mL) was added to the yellow solution and the resulting mixture was extracted with EtOAc (3×100 mL). The combined organics were dried (MgSO4), and solvent was removed in vacuo to give a thick yellow oil which solidified after standing overnight. The crude product was purified by precipitation from EtOAc/hexane to give the title compound (1.70 g, 52%, mp 103-105° C.) as a white solid; δH (270 MHz, CDCl3) 7.42-7.21 (10H, m, ArH), 6.89-6.79 (6H, m, ArH), 5.63 (1H, d, J=3.5, CHOH), 5.06 (4H, s, 2×CH2), 3.86 (6H, s, 2×CH3), 2.02 (1H, d, J=3.5, CHOH); δC (100 MHz, d6-DMSO) 149.2 (2×C), 148.2 (2×C), 137.2 (2×C), 136.6 (2×C), 128.7 (4×CH), 128.0 (2×CH), 127.6 (4×CH), 119.5 (2×CH), 112.6 (2×CH), 111.7 (2×CH), 75.8 (CH), 71.2 (2×CH2), 56.4 (2×CH3); LRMS (FAB+) 456.1 (M+, 45%), 439.1 (85), 349.2 (10), 243.1 (20), 91.1 (100); HRMS (FAB+) Found 456.1944, C29H28O5 requires 456.1937.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at this temperature for 1.5 h
  2. waitat room temperature for 2 h
  3. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organics were dried (MgSO4), and solvent
  5. customwas removed in vacuo
  6. customto give a thick yellow oil which
  7. waitafter standing overnight
  8. customThe crude product was purified by precipitation from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c7c7e93a2d464b61b40020e92c79beed
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

Verknüpfte Notizen

Wird geladen…