Sodium Iodide → Iodomethyl pivalate

HRID 2204058Notes

Reaction equation

HRID 2204058 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

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

  1. customThe mixture was evaporated to dryness
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. washwashed with 5% aqueous NaHSO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe resulting iodomethyl pivalate was used without further purification in the next step

Sources & evidence

ORD record
ord-c47a290abfe347018cde29e7d7b1f8a2
Source dataset
uspto-grants-2016_06
Patent number
US09365605B2

Reaction notes

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