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

HRID 16059

반응식

HRID 16059 반응식
[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]

참가 물질

5

반응물 3

HCID 1183Vanillin2회HCID 7842Propargyl bromideHCID 424914Methyl isonipecotate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-856de8869438445da855a1d4ccaa52da
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737127B2

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