Chlorotrimethylsilane → HCID 15434957, Verbindung

HRID 613402Notizen

Reaktionsgleichung

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](Cl)(C)C.[CH2:16]([C:19]1[CH:40]=[C:39]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:37][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:28][CH:27]=1)[CH2:17][CH3:18].[Br:48]N1C(=O)CCC1=O>C1COCC1>[Br:48][CH:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:20]2[CH:37]=[CH:38][C:39]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:40][C:19]=2[CH2:16][CH2:17][CH3:18])=[CH:27][CH:28]=1)[C:33]([O:35][CH3:36])=[O:34]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of lithium bis(trimethylsilyl)amide (27.36 mL, 27.36 mmol) in dry THF (80 mL) was treated with trimethylsilyl chloride (5.94 mL, 46.76 mmol) at -78° C. To this mixture was added dropwise a solution of the product of Step B (10.80 g, 24.87 mmol) in THF (15 mL). The reaction mixture was stirred at -78° C. for 2 h. N-bromosuccinimide (4.65 g, 26.12 mmol) was added, and the mixture was allowed to warm to room temperature overnight. THF was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed once with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to provide methyl α-bromo-4-(3-(2-propyl-4-phenoxy-phenoxy)propoxy)phenylacetate as an oil.

Aufarbeitung

temperatureto warm to room temperature overnight
customTHF was evaporated
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed once with water
dry with materialdried over sodium sulfate
filtrationThe organic layer was filtered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-94418554259e4a88b0dfccf5b3b8eda9
Quelldatensatz: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06008237

Notizen zur Reaktion

Wird geladen…