1-Bromo-2-Chloroethane → 1-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

HRID 22516

Reaktionsgleichung

Reaktionsgleichung von HRID 22516
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([CH2:16][S:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)([O:13][CH2:14][CH3:15])=[O:12].CN1C[CH2:32][CH2:31]N(C)C1=O.BrCCCl>O1CCCC1>[C:11]([C:16]1([S:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:32][CH2:31]1)([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

6

Edukt 4

HCID 78491-Bromo-2-ChloroethaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 108476441-(Carboethoxy)-1-(4-methoxybenzylthio)methaneHCID 57426343Lithium bis(trimethylsilyl)amide2×

Produkt 1

HCID 224002171-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropaneAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Cool lithium hexamethyldisilazane (6 mL of a 1.0M solution in tetrahydrofuran, 6.0 mmol) to -78° C. Add, by cannula transfer, a solution of 1-(carboethoxy)-1-(4-methoxybenzylthio)methane (1.36 g, 5.66 mmol) in tetrahydrofuran (10 mL). Stir for 45 minutes, add 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (0.73 mL, 6.0 mmol) followed by 1-bromo-2-chloroethane (050 mL, 6.0 mmol) and stir to room temperature overnight. Cool to -78° C., add lithium hexamethyldisilazane (6.0 mL, 6.0 mmol) and stir at room temperature for 24 hours. Quench with saturated ammonium chloride (5 mL) and partition between ethyl acetate (30 mL) and water (30 mL). Separate the organic phase, dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate) to give 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (317 mg, 21%).

Aufarbeitung

  1. additionAdd, by cannula transfer
  2. stirringstir to room temperature overnight
  3. stirringstir at room temperature for 24 hours
  4. customQuench with saturated ammonium chloride (5 mL)
  5. custompartition between ethyl acetate (30 mL) and water (30 mL)
  6. customSeparate the organic phase
  7. dry with materialdry (Na2SO4)
  8. customevaporate the solvent in vacuo
  9. customPurify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-dab25ad53b5e47e6a2206dae9c9bc9f1
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428158

Verknüpfte Notizen

Wird geladen…