Triphenylphosphine → (5-(Ethylamino)-5-oxopentyl)triphenylphosphonium bromide
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][CH2:22][CH2:23][CH2:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26]>CC#N>[Br-:20].[CH2:28]([NH:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][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)[CH3:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Triphenylphosphine (2.88 g, 11 mmol, 1.1 eq.) was added to a solution of 5-bromo-N-ethylpentanamide 95 (2.08 g, 10 mmol, 1 eq.) in MeCN (5 ml) and the mixture was stirred for 14 h at 80° C. The mixture was allowed to cool to r.t. and concentrated under vacuum. The residue was added dropwise into Et2O (100 ml) and stirred vigorously for 10 min. The resulting solid was filtered, washed with Et2O (2×10 ml) and dissolved in CH2Cl2 (15 ml). This solution was then added dropwise into Et2O (200 ml) and stirred for 10 min. Solids were filtered, washed with Et2O (2×10 ml) and dried under high vacuum to give the title product 96 as a white powder (3.87 g, 82%).
Workup
- temperatureto cool to r.t.
- concentrationconcentrated under vacuum
- additionThe residue was added dropwise into Et2O (100 ml)
- stirringstirred vigorously for 10 min
- filtrationThe resulting solid was filtered
- washwashed with Et2O (2×10 ml)
- dissolutiondissolved in CH2Cl2 (15 ml)
- additionThis solution was then added dropwise into Et2O (200 ml)
- stirringstirred for 10 min
- filtrationSolids were filtered
- washwashed with Et2O (2×10 ml)
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-1f321bf795ee4f2babae7bd32fa11833
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242954B2
Reaction notes
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