Diiodomethane → Ethyl 3-iododihydrocinnamate

HRID 129806

반응식

HRID 129806 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 10913723Ethyl 3-iododihydrocinnamate수율 42%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ea6d97466b9452f94debf735e72babc
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

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