Piperidine → HCID 22481762、化合物

HRID 2181659ノート

反応式

HRID 2181659 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][CH3:18])[CH3:14].N1CCCCC1>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[C:17]1[O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH:18]=1)[CH3:14]

参加物

7

反応物 3

HCID 8082PiperidineHCID 20858Propane, 1,1-diethoxy-HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

生成物 1

HCID 22481762HCID 22481762、化合物収率 53.4%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Methyl 4-hydroxy-3-iodo-benzoate (9.9 g, 35 mmol) is combined with propioaldehyde diethylacetal (5.6 ml, 39 mmol), bis(triphenylphosphine)palladium(II) chloride (523 mg, 0.7 mmol), cuprous iodide (266 mg, 1.4 mmol), and piperidine (3.9 ml, 39 mmol) in DMF (50 ml) in a dry flask under nitrogen. The reaction is warmed to 60° C. for 6 h and is stirred overnight at RT. The mixture is diluted with EtOAc (250 ml) and is washed with 2:1:1:0.1 water/brine/saturated NaHCO3/conc. NH4OH (4×100 ml). The organic layer is dried (MgSO4) and is concentrated in vacuo to a dark oil. The crude material is chromatographed over 300 g silica gel (230-400 mesh), eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 5.2 g (48%) methyl 2-(diethoxymethyl)-1-benzofuran-5-carboxylate as an amber oil. HRMS (EI) calcd for C15H18O5: 278.1154, found 278.1156 (M)+.

後処理

  1. washis washed with 2:1:1:0.1 water/brine/saturated NaHCO3/conc
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationis concentrated in vacuo to a dark oil
  4. customThe crude material is chromatographed over 300 g silica gel (230-400 mesh)
  5. washeluting with 15% EtOAc/hexane
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9951192065a64a879b51c98fad56f28f
出典データセット
uspto-grants-2005_05
特許番号
US06894042B2

反応ノート

読み込み中…