Vanillin → Methyl 1-(prop-2-yn-1-yl)piperidine-4-carboxylate

HRID 16059

反応式

HRID 16059 の反応式
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.[CH2:11](Br)[C:12]#[CH:13].O=CC1C=CC(O)=C(OC)C=1>ClCCl>[CH3:8][O:7][C:5]([CH:4]1[CH2:9][CH2:10][N:1]([CH2:13][C:12]#[CH:11])[CH2:2][CH2:3]1)=[O:6]

参加物

5

反応物 3

HCID 1183Vanillin2 回HCID 7842Propargyl bromideHCID 424914Methyl isonipecotate

生成物 1

HCID 58860514Methyl 1-(prop-2-yn-1-yl)piperidine-4-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl isonipecotate 3.5 g (24.4 mmol, 3.30 mL) in 100 mL dichloromethane was added TEA (1.5 eq, 36.6 mmol, 5.1 mL), propargyl bromide (3.0 eq, 73.2 mmol, 6.5 ml), at room temperature for 36 hrs. The reaction was quenched with 35 mL water to yield to provide a clear solution. The solution was extracted with dichloromethane 2×25 mL, dried with Na2SO4, and the solvent evaporated to provide a yellow oil. r.f. (40% EtOAc/Hexanes) 0.26 stains faint white with Vanillin, starting material r.f. 0.05 stains yellow with Vanillin. The product appeared pure after extraction.

後処理

  1. customThe reaction was quenched with 35 mL water
  2. customto yield
  3. customto provide a clear solution
  4. extractionThe solution was extracted with dichloromethane 2×25 mL
  5. dry with materialdried with Na2SO4
  6. customthe solvent evaporated
  7. customto provide a yellow oil
  8. extractionafter extraction

出典と根拠

ORDレコード
ord-856de8869438445da855a1d4ccaa52da
出典データセット
uspto-grants-2010_06
特許番号
US07737127B2

関連ノート

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