Sodium Iodide → 1-Iodoethyl cyclohexyl carbonate

HRID 1361044Notes

Reaction equation

HRID 1361044 reaction equation
[I-:1].[Na+].Cl[CH:4]([O:6][C:7](=[O:15])[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH3:5]>CC#N>[I:1][CH:4]([O:6][C:7](=[O:15])[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH3:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 112295291-Chloroethyl Cyclohexyl Carbonate

Product 1

HCID 111092781-Iodoethyl cyclohexyl carbonateYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium iodide (4.48 g, 29.88 mmol) was dissolved in anhydrous CH3CN (30 mL). Compound 6 (1.20 g, 5.98 mmol) and anhydrous CH3CN (3 mL) were added and stirred for 5.5 hours at 50° C. After filtering and concentration, the residue was diluted with ether and re-concentrated to give 1.21 g of carbonic acid cyclohexyl ester 1-iodo-ethyl ester 7 (Yield: 69%). 1HNMR (CDCl3, 500 MHz) δ 1.25-1.40 (m, 3H), 1.41-1.58 (m, 3H), 1.70-1.78 (m, 2H), 1.85-1.95 (m, 2H), 2.22 (d, J=7.0 Hz, 3H), 4.66-4.71 (m, 1H), 6.77 (q, d=7.0 Hz, 1H).

Workup

  1. filtrationAfter filtering
  2. concentrationconcentration
  3. additionthe residue was diluted with ether
  4. concentrationre-concentrated

Sources & evidence

ORD record
ord-fa379ec53f924cf69a24a13b8285e2af
Source dataset
uspto-grants-2011_02
Patent number
US07879906B2

Reaction notes

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