Dibutyltin oxide → HCID 178497739, Verbindung

HRID 1927397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927397
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[C:7]([Cl:43])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:48]=[N+:49]=[N-:50])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]3[NH:50][N:49]=[N:48][N:40]=3)=[CH:37][CH:38]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)=[C:7]([Cl:43])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831384Methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate

Produkt 1

HCID 178497739HCID 178497739, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 478 mg (0.81 mmol) of methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]-phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate in 10 ml of toluene is mixed with 1116 mg (9.69 mmol) of trimethylsilyl azide and 351 mg (1.21 mmol) of di-n-butyltin oxide and then heated at 80° C. for 12 h. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2). 144 mg (0.23 mmol, 28% of theory) of a white foam are obtained.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe resulting crude product is purified by chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2)
  9. custom144 mg (0.23 mmol, 28% of theory) of a white foam are obtained

Quellen und Nachweise

ORD-Eintrag
ord-21fe4027cded4a4d96428b64f4acb27f
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183271B2

Notizen zur Reaktion

Wird geladen…