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Water → 2-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannane

HRID 1886073
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1886073
C([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:8][N:7]=[N:6]1)(C)(C)C.[Li]C[CH2:19][CH2:20][CH3:21].[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].O.[CH2:37]1COCC1>>[C:20]([N:7]1[NH:6][N:5]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Sn:26]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:23][CH2:24][CH3:25])[NH:8]1)([CH3:19])([CH3:21])[CH3:37]
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Komponenten

6

Edukt 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 15096Tributyltin Chloride2×HCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazoleHCID 178418339Butyllithium

Produkt 1

HCID 676965402-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannane
Ausbeute 45 %

Versuchsvorschrift

To a cooled (-78° C.) solution of 1-tert-butyl-5-(2-bromophenyl)-1H-tetrazole (12.3 g, 0.043 mol), prepared as described in Step 3 of the Example 3 alternative synthesis, in THF (80 mL) was added 1.6M nBuLi in hexanes (32.7 mL, 0.052 mol). After 1 h, tri-n-butyltin chloride (17.1 g, 0.052 mol) was added and stirring was continued for 3 h at -78° C. The mixture was warmed to room temperature and stirred for 18 h. Water was added and the mixture was extracted with ether. The combined extracts were washed with water, brine, dried (MgSO4), and concentrated to give a brown oil. Excess tri-n-butyltin chloride and remaining starting material were removed by distillation under high vacuum to give 9.6 g (45%) of product as a brown oil.

Aufarbeitung

  1. customprepared
  2. waitwas continued for 3 h at -78° C
  3. stirringstirred for 18 h
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customwere removed by distillation under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f64163b983b44d439a5951449609b6f4
Quelldatensatz
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05149699

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