Ammonium Chloride → HCID 59712306, Verbindung

HRID 2222436

Reaktionsgleichung

[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH3:9])=[O:7].C[Si](C)(C)[N-][SiH3].C[Si](C)(C)[N-][SiH3].[Na+].[Na+].[CH:24]([C:26]1[CH:27]=[CH:28][C:29]([O:41][CH3:42])=[C:30]([CH:40]=1)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:25].[Cl-].[NH4+]>O1CCCC1>[C:35]([O:34][C:33]([NH:32][CH2:31][C:30]1[CH:40]=[C:26]([CH:24]([OH:25])[C:2]2([C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:4][CH2:5][O:1]2)[CH:27]=[CH:28][C:29]=1[O:41][CH3:42])=[O:39])([CH3:38])([CH3:36])[CH3:37]

Komponenten

Reaktionsbedingungen

Temperatur: -75 °C

Versuchsvorschrift

A solution of 2.60 g of methyl tetrahydro-2-furancarboxylate in 10 ml of tetrahydrofuran was added dropwise to 20 ml of sodium bis(trimethyldisilylamide) (1 M solution in tetrahydrofuran) cooled to −75° C. under an atmosphere of nitrogen gas, and the reaction mixture was stirred for 30 minutes. A solution of 2.65 g of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate in 20 ml of tetrahydrofuran was added dropwise, and the mixture was stirred further for 1 hour. 200 ml of saturated aqueous ammonium chloride was added, and the mixture was extracted with 200 ml of ethyl acetate. The organic layer washed with 100 ml of brine, dried over magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography, to give 1.934 g of the title compound as a colorless powder.

Aufarbeitung

stirringthe mixture was stirred further for 1 hour
extractionthe mixture was extracted with 200 ml of ethyl acetate
washThe organic layer washed with 100 ml of brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e47bf3d96898477598f20f7da2d75b59
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07371777B2

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