Diiodomethane → Methyl 3-cyclopropylpyridine-2-carboxylate

HRID 1750485ノート

反応式

HRID 1750485 の反応式
ICI.C([Zn]CC)C.[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(C1[C:18]([C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=CC=1)=C>C(Cl)Cl.[Cl-].[NH4+]>[CH:11]1([C:12]2[C:18]([C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

参加物

7

反応物 4

HCID 6346DiiodomethaneHCID 8058HexaneHCID 15257081Methyl 3-ethenylpyridine-2-carboxylateHCID 178418750HCID 178418750、化合物

生成物 1

HCID 68687300Methyl 3-cyclopropylpyridine-2-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

To a stirred solution of diiodomethane (2.46 g, 9.20 mmol) in dry DCM (5 ml) at −10° C. was added diethyl zinc in hexane (1 M, 9.2 ml, 9.20 mmol). The reaction was stirred for 30 minutes under nitrogen. To this was then added methyl 3-ethenylpyridine-2-carboxylate (0.30 g, 1.84 mmol) as a solution in DCM (5 ml) over a 15 minute period. The reaction was then allowed to warm to room temperature and was stirred at room temperature for 15 hours. The reaction mixture was diluted with a saturated solution of ammonium chloride (25 ml) and the organics were extracted with ethyl acetate (3×30 ml). The combined organics were washed with water (25 ml), brine (25 ml), dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane to afford the title compound.

後処理

  1. stirringwas stirred at room temperature for 15 hours
  2. extractionthe organics were extracted with ethyl acetate (3×30 ml)
  3. washThe combined organics were washed with water (25 ml), brine (25 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-492dac1536614cd9a0dc88df3298a9b0
出典データセット
uspto-grants-2015_10
特許番号
US09156829B2

反応ノート

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