Sodium Iodide → Iodomethyl pivalate
Reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Na+].[I-:11]>CC#N>[C:1]([O:7][CH2:8][I:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Chloromethyl pivalate (1.0 mL, 6.90 mmol) was added to a mixture of NaI (2.08 g, 13.80 mmol) and dry MeCN (10 mL). The reaction mixture was stirred at room temperature overnight in the dark. The mixture was evaporated to dryness. The resulting residue was dissolved in dichloromethane and washed with 5% aqueous NaHSO3 and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The resulting iodomethyl pivalate was used without further purification in the next step.
Workup
- customThe mixture was evaporated to dryness
- dissolutionThe resulting residue was dissolved in dichloromethane
- washwashed with 5% aqueous NaHSO3 and brine
- dry with materialThe organic layer was dried over Na2SO4
- customevaporated to dryness
- customThe resulting iodomethyl pivalate was used without further purification in the next step
Sources & evidence
- ORD record
- ord-fd9408826423409db1086e8a791b574d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772474B2
Reaction notes
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