Iodoethane → HCID 68698574, compound

HRID 1990846Notes

Reaction equation

HRID 1990846 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](I)[CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:9][CH2:10][CH2:11][O:12]2)[CH:5]=[C:4]([O:13][CH2:20][CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 68698458HCID 68698458, compound

Product 1

HCID 68698574HCID 68698574, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-[1,3]dioxolan-2-yl-phenol (0.53 g, 2.16 mmol, 1.0 equiv) in DMF (2 mL) was added K2CO3 (0.33 g, 2.38 mmol, 1.1 equiv) and ethyl iodide (0.19 mL, 0.37 g, 2.38 mmol, 1.1 equiv) and the reaction mixture stirred under Ar at rt for 18 h. The K2CO3 was removed by filtration, the filtrate extracted with cyclohexane (3×50 mL), the combined organic phases washed with water (2×50 ml) and dried over MgSO4. The solvent was removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (6:1) providing 0.42 g (72%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.40 (t, J=7.0 Hz, 3H), 4.01-4.10 (m, 6H), 5.75 (s, 1H), 6.93-6.94 (m, 1H), 7.02-7.04 (m, 1H), 7.19-7.20 (m, 1H). MS (EI): 273.0 [M]+.

Workup

  1. customThe K2CO3 was removed by filtration
  2. extractionthe filtrate extracted with cyclohexane (3×50 mL)
  3. washthe combined organic phases washed with water (2×50 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-3c0721ccf62f4d5e8ea81ce205ba5c5a
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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