Ethyl bromoacetate → [6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl ester

HRID 2404202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404202
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1.C([Li])CCC.CCCCCC.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CCOCC>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1)[CH3:40]

Komponenten

6

Edukt 4

HCID 7748Ethyl bromoacetateHCID 8058HexaneHCID 509863542-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 66926519[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl esterAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene (2 g, 5.5 mmol) in ether (10 mL) under nitrogen was added 1.6 M n-butyllithium in hexane (4 mL, 6.4 mmol) at 0° C. The solution was stirred for 30 min at 0° C., then treated with copper(I) bromide-dimethyl sulfide complex (0.8 g, 3.9 mmol). After 2 hrs stirring, a solution of ethyl bromoacetate (0.7 mL, 6 mmol) in ether (4 mL) was added. The solution was stirred at 0° C. for 2 hrs, then warmed to room temperature for 3 hrs. The reaction was quenched with 10% HCl aqueous then the insoluble was filtered off. The organic layer was washed with water, sodium bicarbonate aqueous, dried over MgSO4, filtered and concentrated. The crude was purified via silica gel column eluted with EtOAc in hexanes from 0 to 10% to give light yellow solid (0.45 g, yield: 22% yield). ESI-MS: 369.20 (M+H)+.

Aufarbeitung

  1. additiontreated with copper(I) bromide-dimethyl sulfide complex (0.8 g, 3.9 mmol)
  2. stirringAfter 2 hrs stirring
  3. stirringThe solution was stirred at 0° C. for 2 hrs
  4. temperaturewarmed to room temperature for 3 hrs
  5. customThe reaction was quenched with 10% HCl aqueous
  6. filtrationthe insoluble was filtered off
  7. washThe organic layer was washed with water, sodium bicarbonate aqueous
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude was purified via silica gel column
  12. washeluted with EtOAc in hexanes from 0 to 10%

Quellen und Nachweise

ORD-Eintrag
ord-70394fa315cc47759e0723186e743d2c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

Notizen zur Reaktion

Wird geladen…