Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH3:25][O:24][C:22](=[O:23])[CH:21]([O:20][CH3:19])[CH:13]([C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:17][CH3:18])[CH:11]=1)[OH:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 4-benzyloxy-3-methoxy-benzaldehyde (0.44 g, 1.92 mmol) and methyl methoxyacetate (0.19 mL, 1.92 mmol) in THF (10 mL) at −78° C. was added dropwise to sodium bis(trimethylsilyl)amide (20 mL, 2.11 mmol, 1N in THF) at −78° C. The reaction mixture was stirred for 3 h and quenched with 1N HCl (5 mL). The mixture was allowed to warm to room temperature, diluted with water (15 mL), and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 1:1) to produce 3-(4-benzyloxy-3-methoxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester as an oil (350 mg, 52%); 1H-NMR (200.15 MHz, CDCl3): δ 7.45–7.20 (m, 5H), 6.9 (s, 1H), 6.8 (b, 2H), 5.1 (s, 2H), 4.90–4.80 (m, 1H), 4.10 (m, 1H), 3.90 (s, 3H), 3.65 (s, 3H), 3.31 (s, 3H), 3.10–2.96 (m, 1H).
Aufarbeitung
- customquenched with 1N HCl (5 mL)
- additiondiluted with water (15 mL)
- extractionextracted with ethyl acetate (3×15 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-60889b9d44984c7bb7085c111dcab2e9
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07192982B2
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