Tetrahydrofuran → HCID 54165665, Verbindung

HRID 2293698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293698
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][OH:7])=[CH:2]1.[CH2:8]([Li])CCC.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH:13]1([CH:17]([C:5]2[S:1][C:2]([CH3:8])=[C:3]([CH2:6][OH:7])[CH:4]=2)[OH:16])[CH2:14][CH2:15]1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 123570Thiophene-3-methanolHCID 178418339Butyllithium

Produkt 1

HCID 54165665HCID 54165665, Verbindung

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Thiophene-3-methanol of formula UU-1 (4.56 g) is added to THF (100 mL) and cooled to -78° C. n-Butyl lithium (55 cc) is then added and the reaction stirred for 2 hours at -78° C. and then the cooling bath is removed for 30 minutes. The reaction temperature is again reduced to -78° C. and methyl iodide (5.68 g), in THF (5 mL), is added. The reaction is stirred for 1.3-1.0 hours at room temperature and then cooled back to -78° C. n-Butyl lithium is then added and the reaction is left stirring for 1 hour at -78° C. and then the cooling bath removed for 30 minutes and cooled back to -78° C. Cyclopropyl carboxaldehyde (2.8 g) is then added in a single portion and stirring continued for 30 minutes. The reaction is quenched with saturated NH4Cl and extracted with ether. The ether extracts are dried and solvent evaporated in vacuo to yield a pale brown oil. Silica gel chromatography (400 g silica gel; eluting with 1/1 EtOAc/hexane) affords 1.21 g of the title product.

Aufarbeitung

  1. additionis then added
  2. customthe cooling bath is removed for 30 minutes
  3. customis again reduced to -78° C.
  4. additionmethyl iodide (5.68 g), in THF (5 mL), is added
  5. stirringThe reaction is stirred for 1.3-1.0 hours at room temperature
  6. temperaturecooled back to -78° C. n-Butyl lithium
  7. additionis then added
  8. waitthe reaction is left
  9. stirringstirring for 1 hour at -78° C.
  10. customthe cooling bath removed for 30 minutes
  11. temperaturecooled back to -78° C
  12. additionCyclopropyl carboxaldehyde (2.8 g) is then added in a single portion
  13. stirringstirring
  14. waitcontinued for 30 minutes
  15. customThe reaction is quenched with saturated NH4Cl
  16. extractionextracted with ether
  17. dry with materialThe ether extracts are dried
  18. customsolvent evaporated in vacuo
  19. customto yield a pale brown oil
  20. washSilica gel chromatography (400 g silica gel; eluting with 1/1 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-985af3b2edef4c4f8a2e73f7050a829f
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686486

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