Boron trifluoride → 1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

HRID 351435

Reaktionsgleichung

Reaktionsgleichung von HRID 351435
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)=[CH2:18])=[CH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][C:34](=[CH2:37])[CH:35]=[O:36].B(F)(F)F>C(Cl)Cl>[CH3:33][C:34]1([CH:35]=[O:36])[CH2:37][CH2:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][CH:24]=2)[CH2:18]1

Komponenten

5

Edukt 3

HCID 6356Boron trifluorideHCID 6562MethacroleinHCID 184363312,3-Di(4-benzyloxy-phenyl)-1,3-butadiene

Produkt 1

HCID 865958461-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,3-di(4-benzyloxy-phenyl)-1,3-butadiene (1.2 g, 2.8 mmol) and 2-methyl-propenal (0.602 g, 8.4 mmol) in DCM (10.5 mL) was added BF3.OCH2CH3 (0.596 mL, 4.2 mmol) at −10° C. After 3 h at −10° C., the reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL). The reaction mixture was then extracted with ethyl acetate (2 10 mL), dried over MgSO4 and purified by SiO2 twice (15% ethyl acetate/hexane) to yield 1-methyl-3,4-di(4-benzyloxy-phenyl )-cyclohex-3-ene carbaldehyde.

Aufarbeitung

  1. customat −10° C
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe reaction mixture was then extracted with ethyl acetate (2 10 mL)
  4. dry with materialdried over MgSO4
  5. custompurified by SiO2 twice (15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cccc71e19d034744869a56f0a372cf5c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183445B2

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