Methyl iodide → Methyl 5-bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylate
Reaktionsgleichung
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]([CH:15]1[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14].I[CH3:26]>C1COCC1>[CH3:11][O:12][C:13]([C:15]1([CH3:26])[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Lithium bis(trimethylsilyl)amide (6.16 ml, 6.16 mmol, 1M solution in THF) was added dropwise to a solution of (rac)-5-bromo-indan-1-carboxylic acid methyl ester (1.31 g, 5.14 mmol) in dry THF (25 ml) at −78° C. After the addition was completed, the solution was stirred at −78° C. for 45 minutes. Then, iodomethane (2.19 g, 959 μl, 15.4 mmol) was added, the solution was allowed to warm to room temperature and stirred for 48 h. The reaction was quenched by addition of sat. NH4Cl solution and extracted two times with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as yellow oil (1.319 g, 95%). MS: 269.2 [M+H]+.
Aufarbeitung
- additionAfter the addition
- temperatureto warm to room temperature
- stirringstirred for 48 h
- customThe reaction was quenched by addition of sat. NH4Cl solution
- extractionextracted two times with EtOAc
- washThe combined organic layers were washed with brine
- dry with materialdried with Na2SO4
- customevaporated
- customThe remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)
Quellen und Nachweise
- ORD-Eintrag
- ord-708f1d7cb6334aa4a012cc8157bc2c14
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08592426B2
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