2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 1-(Carboethoxy)-1-(4-methoxybenzylthio)cyclohexane

HRID 375555

Reaktionsgleichung

Reaktionsgleichung von HRID 375555
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].I[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Cl.CN1CCCN(C)C1=O>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][CH2:30][CH2:29][CH2:28]1)([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

6

Edukt 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 1089141-Chloro-5-iodopentaneHCID 108476441-(Carboethoxy)-1-(4-methoxybenzylthio)methaneHCID 57426343Lithium bis(trimethylsilyl)amide2×

Produkt 1

HCID 224002131-(Carboethoxy)-1-(4-methoxybenzylthio)cyclohexaneAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Cool lithium hexamethyldisilazane (8.4 mL of a 1.0M solution in tetrahydrofuran, 8.4 mmol) to -78° C. Add , by cannula transfer, a solution of 1-(carboethoxy)-1-(4-methoxybenzylthio)methane (2.0 g, 8.3 mmol) in tetrahydrofuran (8 mL). Stir for 45 minutes then add a solution of 1-iodo-5-chloropentane (1.94 g, 8.32 mmol) in tetrahydrofuran (8 mL). Stir for 1 hour and add 1,3-dimethyl-3,4,5, 6-tetrahydro -2(1H)-pyrimidinone (DMPU) (1.21 mL, 10.0 mmol). Stir at 0° C. for 4 hours and at room temperature for 6 hours. Cool to -78° C., add lithium hexamethyldisilazane (8.4 mL, 8.4mmol) and stir at room temperature overnight. Quench with saturated ammonium chloride (5 mL) and partition between ethyl acetate (50 mL) and water (50 mL). Separate the organic phase, dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (6:1 hexane/ethyl acetate) to give 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclohexane as an colorless oil (1.45 g, 56%).

Aufarbeitung

  1. additionAdd , by cannula transfer
  2. stirringStir for 1 hour
  3. stirringStir at 0° C. for 4 hours and at room temperature for 6 hours
  4. stirringstir at room temperature overnight
  5. customQuench with saturated ammonium chloride (5 mL)
  6. custompartition between ethyl acetate (50 mL) and water (50 mL)
  7. customSeparate the organic phase
  8. dry with materialdry (Na2SO4)
  9. customevaporate the solvent in vacuo
  10. customPurify by chromatography (6:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0958d114d8864b7a8c2a5245205c059d
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486513

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