Acetonitrile → [1-Hydroxy-(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]phosphonic acid
Reaction equation
[OH:1][CH:2]([P:18](=[O:25])([O:22]CC)[O:19]CC)[CH2:3]/[CH:4]=[C:5](\[CH3:17])/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].N1C(C)=CC(C)=CC=1C.C[Si](Br)(C)C.C(#N)C>ClCCl.C1(C)C=CC=CC=1>[OH:1][CH:2]([P:18](=[O:19])([OH:25])[OH:22])[CH2:3]/[CH:4]=[C:5](\[CH3:17])/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of diethyl [1-hydroxy-(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]phosphonate (37 mg, 0.0993 mmol) and 2,4,6-collidine (0.052 ml, 0.397 mmol) in dichloromethane (3 ml) under argon at 0° C., was added trimethylsilyl bromide (0.052 ml, 0.397 mmol) and the resulting mixture stirred at 0° C. for 30 min and then at r.t. for 4 hr. The resulting white suspension was diluted with toluene (10 ml) and the solvent evaporated in vacuo. The resulting white solid was dissolved in ethylacetate and water and the pH was adjusted to 3 by the addition of 1M HCl solution. The organic layer was separated and dried (MgSO4) and evaporated to afford a clear oil. Addition of acetonitrile 2 ml precipitated the title compound as an off white solid which was removed by filtration and dried in vacuo.
Workup
- waitat r.t. for 4 hr
- customthe solvent evaporated in vacuo
- dissolutionThe resulting white solid was dissolved in ethylacetate
- additionwater and the pH was adjusted to 3 by the addition of 1M HCl solution
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- customevaporated
- customto afford a clear oil
- customprecipitated the title compound as an off white solid which
- customwas removed by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-5aee9ec29ba54fd7938bae042940861d
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05362906
Reaction notes
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