Diiodomethane → Ethyl 3-iododihydrocinnamate

HRID 129806ノート

反応式

HRID 129806 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 10913723Ethyl 3-iododihydrocinnamate収率 42%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5ea6d97466b9452f94debf735e72babc
出典データセット
uspto-grants-1995_11
特許番号
US05470845

反応ノート

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