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

HRID 1644583

反応式

HRID 1644583 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1567ed6032804ef2a8faf4a7aa64cbdf
出典データセット
uspto-grants-2012_02
特許番号
US08124617B2

関連ノート

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