Diethyl Malonate → Diethyl 2-(1-Bromo-2-naphthylmethyl)malonate

HRID 1290319

Reaktionsgleichung

Reaktionsgleichung von HRID 1290319
CC[O-].[Na+].[Na].[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28]Br>O.C(Cl)Cl.CCO>[Br:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

8

Edukt 4

HCID 7761Diethyl MalonateHCID 378281-Bromo-2-(bromomethyl)naphthaleneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 14491492Diethyl 2-(1-Bromo-2-naphthylmethyl)malonateAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of NaOEt prepared from 9.66 g of sodium and 210 mL of dry EtOH was added 63.76 mL of diethyl malonate and the reaction mixture refluxed for 2 h. To the resulting yellow solution was added in small portions 126 g of 1-bromo-2-bromomethylnaphthalene and the reaction mixture refluxed for 16 h. Distillation of ethanol from an oil bath (100°-110° C.) through a simple Claisen head gave a yellow suspension, to which was added 350 mL of CH2Cl2 and 350 mL of H2O. The aqueous layer was extracted twice with 120-mL portions of CH2Cl2, and the combined organic layer was washed three times with 100-mL portion of H2O, dried (MgSO4) and evaporated to give 152 g (95.6%) of the ester as a yellow solid, mp 60°-65° C. Recrystallization from acetic acid gave 137 g (86.2%) of the pure diester as a colorless solid, mp 77°-79° C.

Aufarbeitung

  1. temperaturethe reaction mixture refluxed for 2 h
  2. temperaturethe reaction mixture refluxed for 16 h
  3. distillationDistillation of ethanol from an oil bath (100°-110° C.) through a simple Claisen head
  4. customgave a yellow suspension
  5. extractionThe aqueous layer was extracted twice with 120-mL portions of CH2Cl2
  6. washthe combined organic layer was washed three times with 100-mL portion of H2O
  7. dry with materialdried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-edce69a42435422ba59d585e8c0d274a
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750767

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