Diphenylphosphinic chloride → 4-[2-(4-Geranyloxybenzoylamino)ethyl]pyridine

HRID 850400ノート

反応式

HRID 850400 の反応式
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[O:18])=[CH:19][CH:20]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]

参加物

6

反応物 3

HCID 73910Diphenylphosphinic chlorideHCID 832754-PyridineethanamineHCID 123615004-Geranyloxybenzoic acid

生成物 1

HCID 99296694-[2-(4-Geranyloxybenzoylamino)ethyl]pyridine収率 85.3%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

実験手順

4-geranyloxybenzoic acid(1.92 g) was dissolved in chloroform(50 ml) and triethylamine(1.96 ml), and then diphenylphosphinic chloride(1.33 ml) was added thereto while being cooled with ice. After being stirred for 30 minutes, the mixture, with 4-(2-aminoethyl)pyridine(0.94 g) added thereto, was stirred for 2 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1), thereby yielding 2.26 g of the aimed compound.

後処理

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 2 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

出典と根拠

ORDレコード
ord-548c05eaa5b944c19c87e05f69f48e27
出典データセット
uspto-grants-2000_01
特許番号
US06017937

反応ノート

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