Tributylphosphine → Methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate

HRID 1644583

반응식

HRID 1644583 반응식
[OH:1][C:2]1[CH:3]=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH2:23][CH2:24]O)[CH:17]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1.CCCCCC>[CH:13]([O:12][C:4]1[CH:5]=[C:6]([CH:11]=[C:2]([O:1][CH2:24][CH2:23][CH2:22][C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:15])[CH3:14]

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 178613-PyridinepropanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

생성물 1

HCID 66775698Methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate수율 86.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution (60 ml) of methyl 5-hydroxy-3-isopropoxybenzoate (2.0 g) and 3-(pyridin-3-yl)propanol (1.6 g) in THF were added successively 1,1′-(azodicarbonyl)dipiperidine (2.9 g) and tributylphosphine (2.8 ml) under ice-cooling, and the mixture was stirred overnight at room temperature. n-Hexane (100 ml) was added to the reaction mixture, and the precipitated crystals were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (LL, Biotage cartridge, ethyl acetate:n-hexane=15:85→1:4) to give methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate (2.70 g, 86%) as a colorless oil.

후처리

  1. temperaturecooling
  2. customthe precipitated crystals were removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography (LL, Biotage cartridge, ethyl acetate:n-hexane=15:85→1:4)

출처 및 근거

ORD 기록
ord-1567ed6032804ef2a8faf4a7aa64cbdf
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124617B2

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