Triphenylphosphine → 2E-5-trimethylsilylpent-2-en-4-ynyltriphenylphosphonium bromide

HRID 1671729

Reaktionsgleichung

Reaktionsgleichung von HRID 1671729
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH:22]=[CH:23][C:24]#[C:25][Si:26]([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1.C(OC)(C)(C)C>[Br-:20].[CH3:27][Si:26]([CH3:29])([CH3:28])[C:25]#[C:24]/[CH:23]=[CH:22]/[CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 572808031-Bromo-5-trimethylsilylpent-2-en-4-yne

Produkt 1

HCID 111558512E-5-trimethylsilylpent-2-en-4-ynyltriphenylphosphonium bromideAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

Triphenylphosphine (64.1 g, 0.244 mol) was added to a solution of 1-bromo-5-trimethylsilylpent-2-en-4-yne (44.26 g, 0.204 mol) in toluene (204 mL). The mixture was stirred at ambient temperature under a nitrogen atmosphere. After 3 days the suspension was diluted with methyl tert-butyl ether (408 mL), stirred for 1 hour at ambient temperature, and the precipitate was collected by filtration. The filter cake was washed with methyl tert-butyl ether and dried under vacuum at 30° C. to get 79 g of 2E-5-trimethylsilylpent-2-en-4-ynyltriphenylphosphonium bromide, a compound of formula (Q), as an off-white powder: 1H-NMR (300 mHz, CDCl3) 6 0.14 (s, 9H), 5.08 (dd, 2H), 5.91 (dt, 1H), 6.22 (dd, 1H), 7.6-8.0 (m, 15 H); Anal. Calculated for C26H28BrPSi requires C 65.13, H 5.89, Br 16.66, P 6.46; found C 64.95, H 5.78, Br 16.96, P 6.31.

Aufarbeitung

  1. stirringstirred for 1 hour at ambient temperature
  2. filtrationthe precipitate was collected by filtration
  3. washThe filter cake was washed with methyl tert-butyl ether
  4. customdried under vacuum at 30° C.

Quellen und Nachweise

ORD-Eintrag
ord-b8202acdd00a40d4b0c2d96ac67c16e6
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994346B2

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