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

HRID 892181노트

반응식

HRID 892181 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
85 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e80f982d165441a790011ce87428323f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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