Sodium hydride → HCID 22285400, Verbindung

HRID 1062457

Reaktionsgleichung

Reaktionsgleichung von HRID 1062457
[H-].[Na+].Br[CH2:4][CH:5]1[CH2:7][CH2:6]1.[S:8]1[CH2:13][CH2:12][CH2:11][S:10][CH:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1.CN(C=O)C>[CH:7]1([CH2:6][C:9]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:8][CH2:13][CH2:12][CH2:11][S:10]2)[CH2:5][CH2:4]1

Komponenten

6

Edukt 3

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

Produkt 1

HCID 22285400HCID 22285400, VerbindungAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of NaH (95%, 2.8 g, 111 mmol) in dry toluene (120 mL) stirring at 0° C. was dropwise added, over 10 minutes, a solution of bromomethylcyclopropane (15 g, 111 mmol), and ethyl 1,3-dithiane-2-carboxylate (17.77 g, 92.58 mmol) in dry DMF (40 mL). The ice bath was removed and the solution was stirred overnight at rt. Water was added to the solution and the phases were separated. The organic phase was dried over MgSO4, then evaporated to give 19.6 g (50%) of ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate, which was used in the next step without purification. 1H NMR (CDCl3): δ 4.26 (2H, q, J=7.2 Hz), 3.30-3.23 (2H, m), 2.69-2.64 (2H, m), 2.16-2.11 (1H, m), 1.96 (2H, d, J=6.8 Hz), 1.91-1.81 (1H, m), 1.34 (3H, t, J=7.2 Hz), 0.93-0.86 (1H, m), 0.52-0.47 (2H, m), 0.20-0.16 (2H, m).

Aufarbeitung

  1. additionwas dropwise added, over 10 minutes
  2. customThe ice bath was removed
  3. stirringthe solution was stirred overnight at rt
  4. additionWater was added to the solution
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried over MgSO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1cc0038cd33940ad9679aa17d7e8acb5
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960601B2

Verknüpfte Notizen

Wird geladen…