Reaktionsgleichung
[OH:1][C@H:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][O:4][C:3]1=[O:9].C(N(C(C)C)CC)(C)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].Cl>ClCCl.CCOC(C)=O>[CH3:7][C:6]1([CH3:8])[CH2:5][O:4][C:3](=[O:9])[CH:2]1[O:1][C:19](=[O:22])[CH:20]=[CH2:21]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) was prepared in the following manner: 3-(S)-Hydroxy-4,4-dimethyl-dihydro-furan-2-one (2.60 g, 20 mmol) and diisopropylethylamine (5.2 mL, 30 mmol) in dichloromethane (25 mL) was cooled to −10° C. and treated dropwise with acryloyl chloride (2.03 mL, 25 mmol) and stirred for 2 h. 1M HCl (20 mL) was added and the organic layer was washed with sodium bicarbonate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography (10-40% EtOAc, hexanes) afforded 2.09 g (57% yield) of the desired acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) as a clear oil. This substrate was used to prepare the acid chloride of (1R)-4-methyl-cyclohex-3-enecarboxylic acid analogous to the procedure described in Scheme 15 and Scheme 16.
Aufarbeitung
- customAcrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) was prepared in the following manner
- washthe organic layer was washed with sodium bicarbonate and water
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-d1c46801d9a049babb27b3a99eb86b82
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08513298B2
Verknüpfte Notizen
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