Dimethylformamide → 2,2-Dimethyl-4(tol-4-yl)-thiochrom-3-en-6-al

HRID 2288308

Reaktionsgleichung

Reaktionsgleichung von HRID 2288308
[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[S:3]1.[Li]CCCC.CN([CH:29]=[O:30])C>C1COCC1.CCCCCC>[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:29]=[O:30])[CH:8]=2)[S:3]1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 861914872,2-Dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene2×HCID 178418339Butyllithium

Produkt 1

HCID 158872822,2-Dimethyl-4(tol-4-yl)-thiochrom-3-en-6-al

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene (Compound N, 280 mg, 0.81 mmol) in THF (5 mL) was added n-BuLi in hexane (1.6 M solution, 0.66 mL). The mixture was gradually warmed to -10° C. over 25 min. and recooled to -78° C. To this solution was added DMF (80 mg, 1.1 mmol) and stirred at ambient temperature for 5 hours. The reaction was quenched by adding water (10 mL), ethyl acetate (100 mL), and the organic layer was washed with brine (10 mL), dried and the solvent removed by distillation. The crude material was used in the next reaction without further purification.

Aufarbeitung

  1. customrecooled to -78° C
  2. customThe reaction was quenched
  3. additionby adding water (10 mL), ethyl acetate (100 mL)
  4. washthe organic layer was washed with brine (10 mL)
  5. customdried
  6. customthe solvent removed by distillation
  7. customThe crude material was used in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-dc2a6349e3fa4cfc88f7dfc7b7be2995
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087505

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