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

HRID 2078495Notes

Reaction equation

HRID 2078495 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 111558512E-5-trimethylsilylpent-2-en-4-ynyltriphenylphosphonium bromideYield 80.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

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-ynyltriphenyl-phosphonium bromide, a compound of formula (Q), as an off-white powder: 1H-NMR (300 mHz, CDCl3) δ 0.14 (s, 9H), 5.08 (dd, 2H), 5.91 (dt, 1H), 6.22 (dd, 1H), 7.6-8.0 (m, 15H); 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.

Workup

  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.

Sources & evidence

ORD record
ord-0501bfa80f0c406cb4ca134603ed7df2
Source dataset
uspto-grants-2011_04
Patent number
US07928255B2

Reaction notes

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