Hexachloroethane → Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-yl ester

HRID 450293

Reaktionsgleichung

[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.C([Li])(CC)C.[Cl:38]C(Cl)(Cl)C(Cl)(Cl)Cl.[Cl-].[NH4+]>C1COCC1>[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[C:10]([Cl:38])[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester (9.26 g, 26.7 mmol) is dissolved in THF (250 mL), flushed with nitrogen and cooled to −78° C. TMEDA (5 mL, 33.1 mmol) is then added followed by sec-butyllithium (24.8 mL, 34.7 mmol) and the reaction is stirred for 30 minutes. Hexachloroethane (12.73 g, 53.8 mmol) in 50 mL of THF is added over 10 minutes to the reaction. The reaction is allowed to warm to room temperature overnight (15 hours). The reaction is cooled using an ice bath and a saturated ammonium chloride (aq) solution is added (150 mL). The mixture is then extracted with ethyl acetate, dried (sodium sulfate) and concentrated to obtain the title compound as an oil that is used without further purification. MS (ESI) m/z 381.1 (M+1).

Aufarbeitung

customflushed with nitrogen
temperatureto warm to room temperature overnight (15 hours)
temperatureThe reaction is cooled
extractionThe mixture is then extracted with ethyl acetate
dry with materialdried (sodium sulfate)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-ed2e015faf7148bebe191541f8f80ee1
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08486954B2

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