Diiodomethane → Ethyl 3-iododihydrocinnamate

HRID 865877Notes

Reaction equation

HRID 865877 reaction equation
N[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[I:15]CI.N(OCCC(C)C)=O>C(OCC)C>[I:15][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 82314Ethyl 3-(3-Aminophenyl)propionate

Product 1

HCID 10913723Ethyl 3-iododihydrocinnamateYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of Part (2) compound (7.2 g, 32 mmol) in diiodomethane (10.3 mL, 128 mmol) under argon at RT was added isoamyl nitrite (6.5 mL, 64 mmol) over 10 min. The brownish solution was stirred at RT for 40 min and then heated to 80° C. for 2 h. Ethyl ether (300 mL) was added to the reaction and the organic layer was washed with 1N hydrochloric acid (70 mL×2), water (70 mL), saturated sodium bicarbonate (70 mL×2), 10% sodium bisulfite solution (30 mL) and dried over magnesium sulfate. Purification was performed by flash chromatography on 800 g silica gel, loaded and eluted with 7% ethyl acetate in hexane. Pure, fractions were combined and evaporated to give the title compound (4.1 g, 42%) as a colorless oil.

Workup

  1. temperatureheated to 80° C. for 2 h
  2. washthe organic layer was washed with 1N hydrochloric acid (70 mL×2), water (70 mL), saturated sodium bicarbonate (70 mL×2), 10% sodium bisulfite solution (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. customPurification
  5. washeluted with 7% ethyl acetate in hexane
  6. customevaporated

Sources & evidence

ORD record
ord-822fef603f2c408595f5100c0f0ab360
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Reaction notes

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