Sodium Iodide → Propanoic acid, 2-methyl-, 1-iodoethyl ester

HRID 1361045Notes

Reaction equation

HRID 1361045 reaction equation
[I-:1].[Na+].Cl[CH:4]([O:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])[CH3:5]>CC#N>[I:1][CH:4]([O:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])[CH3:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131387431-Chloroethyl 2-methylpropanoate

Product 1

HCID 14633820Propanoic acid, 2-methyl-, 1-iodoethyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Sodium iodide (4.5 g, 29.43 mmol) was dissolved in CH3CN (13 mL). Compound 13 (2.16 g, 14.4 mmol) and CH3CN (5 mL) were added and stirred for 6.5 hours. After filtering and concentrating, the reaction solution was diluted with ether (10 mL) and then re-concentrated to give 1.597 g of isobutyric acid 1-iodo-ethyl ester 14 (Yield: 46%). 1HNMR (CDCl3, 500 MHz) δ1.16-1.21 (m, 6H), 2.20 (d, J=5.5 Hz, 3H), 2.45-2.61 (m, 1H), 6.86 (q, J=6.0 Hz, 1H).

Workup

  1. filtrationAfter filtering
  2. concentrationconcentrating
  3. additionthe reaction solution was diluted with ether (10 mL)
  4. concentrationre-concentrated

Sources & evidence

ORD record
ord-ee64fc1c732b4f81b3a46c6f24c5c055
Source dataset
uspto-grants-2011_02
Patent number
US07879906B2

Reaction notes

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