Benzyl Bromide → Benzyl 6-heptenoate

HRID 605573

Reaktionsgleichung

Reaktionsgleichung von HRID 605573
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOC(C)=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[C:1]([O:9][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 707056-Heptenoic acid

Produkt 1

HCID 14741231Benzyl 6-heptenoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-heptenoic acid (4.71 g, 36.75 mmol) in AcOEt (80 mL) at 0° C. were successively added triethylamine (15.3 mL, 110.24 mmol), benzyl bromide (13.1 mL, 110.24 mmol) and Bu4NI (6.79 g, 18.37 mmol). The reaction mixture was stirred at 0° C. for 2H and concentrated in vacuo. The residue is taken up in AcOEt, the organic phase was washed with a saturated aqueous NaHCO3 and H2O. The organic phase was dried over MgSO4 and the solvent removed in vacuo. Flash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound C-9 (6.00 g 75%) as a colorless oil. 13C-NMR (62.89 MHz, CDCl3): 24.42, 28.34, 33.37, 34.13, 66.08, 114.73, 128.19, 128.55, 136.16, 138.37, 173.43.

Aufarbeitung

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. washthe organic phase was washed with a saturated aqueous NaHCO3 and H2O
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent removed in vacuo
  6. customFlash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound C-9 (6.00 g 75%) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-6db620ee6cfe4d1fa9f80f861b1d3444
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915240B2

Verknüpfte Notizen

Wird geladen…