Toluene → HCID 22285400, Verbindung

HRID 1689751

Reaktionsgleichung

Reaktionsgleichung von HRID 1689751
[C:1]1([CH3:7])[CH:6]=[CH:5]C=CC=1.[H-].[Na+].[S:10]1[CH2:15][CH2:14][CH2:13][S:12][CH:11]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].BrCC1CC1>CN(C=O)C>[CH2:19]([O:18][C:16]([C:11]1([CH2:7][CH:1]2[CH2:6][CH2:5]2)[S:12][CH2:13][CH2:14][CH2:15][S:10]1)=[O:17])[CH3:20]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 88552Ethyl 1,3-dithiane-2-carboxylate

Produkt 1

HCID 22285400HCID 22285400, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flamed dried flask is added dry toluene (80 mL) and sodium hydride (60%, 33.5 mmol, 1.34 g). The reaction is cooled in a ice bath and a solution of ethyl 1,3 dithiane carboxylate (52 mmol, 10 g) and bromomethyl cyclopropane (62.4 mmol, 8.42 g) in DMF (24 mL) are added dropwise over 10 minutes. The ice bath is removed and the reaction is stirred for 18 h. Water is added (50 mL) and the organic layer is separated. The organic layer is washed with brine, dried (Na2SO4), and concentrated to a yellow oil (12 g, 92%). LC-ES/MS: 247.0 (M+1).

Aufarbeitung

  1. customTo a flamed dried flask
  2. temperatureThe reaction is cooled in a ice bath
  3. customThe ice bath is removed
  4. additionWater is added (50 mL)
  5. customthe organic layer is separated
  6. washThe organic layer is washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to a yellow oil (12 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-2b7089650b25413781be88d029022323
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153624B2

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