Reaktionsgleichung
[CH2:1]([C:3](=[CH2:6])[CH:4]=[O:5])[CH3:2].[SH:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].C(N(CC)CC)C>C1COCC1.CCOCC>[C:10]([C:9]1[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=1[S:7][CH2:6][CH:3]([CH2:1][CH3:2])[CH:4]=[O:5])(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To an ice bath cooled solution of 9.76 g (0.116 mole) of 2-ethylacrolein in 40 mL of dry THF was added 24.6 g (0.116 mole) of 2-mercaptobenzophenone in 40 mL of THF followed by 13 g, (0.128 mole) of triethylamine. The reaction mixture was stirred at room temperature for 3 days, diluted with ether, and was washed successively with dilute HCl, brine, and 1 M potassium carbonate. The ether layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by HPLC (10% EtOAc-hexane) to give 22 g (64%) of 11 in the second fraction. An attempt to further purify this material by kugelrohr distillation at 0.5 torr (160-190° C.) gave a fraction (12.2 g) which contained starting material indicating a reversed reaction during distillation. This material was dissolved in ether (100 mL) and was washed with 50mL of 1 M potassium carbonate three times to give 6.0 g of a syrup which was purified by HPLC (10% EtOAc-hexane) to give 5.6 g of pure 11.
Aufarbeitung
- washwas washed successively with dilute HCl, brine, and 1 M potassium carbonate
- dry with materialThe ether layer was dried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by HPLC (10% EtOAc-hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-65e628fab7e4417b981e4e8fa649ae8e
- Quelldatensatz
- uspto-grants-2003_11
- Patentnummer
- US06642268B2
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