Malonic Acid → 3-{2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-phenyl}-acrylic acid

HRID 892181ノート

反応式

HRID 892181 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=1)[CH2:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.C(O)(=O)[CH2:30][C:31]([OH:33])=[O:32].N1CCCCC1>N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=1)[CH2:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=[CH:30][C:31]([OH:33])=[O:32]

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 222412772-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

生成物 1

HCID 696601643-{2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-phenyl}-acrylic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
85 °C

実験手順

2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde (110 mg, 0.3 mmol, example 56) is dissolved in pyridine (1 mL). Malonic acid (63 mg, 0.6 mmol) and piperidine (10 μL, 0.1 mmol) are added and the contents are heated to 85° C. for 2 hrs, then at 110° C. for another 2 hrs. The reaction is cooled and placed under a nitrogen stream at 40° C. to remove the pyridine. A small amount of toluene is added and the contents are again placed under a nitrogen stream at 40° C. (repeat). The crude material is purified on silica gel by flash chromatography (silica, 2.5% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.33 (d, 1H), 8.21–8.16 (m, 2H), 7.81–7.70 (m, 3H), 7.56–7.50 (m, 2H), 7.37–7.25 (m, 3H), 7.03–6.93 (m, 4H), 6.50 (d, 1H), 5.48 (s, 2H), 5.14 (s, 2H); MS (ion spray) 412 (M+H)+.

後処理

  1. temperatureThe reaction is cooled
  2. customat 40° C.
  3. customto remove the pyridine
  4. additionA small amount of toluene is added
  5. customat 40° C.
  6. customThe crude material is purified on silica gel by flash chromatography (silica, 2.5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-e80f982d165441a790011ce87428323f
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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