1-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid → 1-(Benzofuran-5-yl)cyclopropanecarboxylic acid

HRID 503242

반응식

HRID 503242 반응식
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C>C1(C)C(C)=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]3)=[CH:9][C:8]=2[CH:4]=[CH:5]1

참가 물질

3

반응물 1

HCID 591292871-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid

생성물 1

HCID 513584541-(Benzofuran-5-yl)cyclopropanecarboxylic acid수율 11.4%

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
140 °C

실험 절차

To a suspension of 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (20 g, ˜65 mmol) in xylene (100 mL) was added PPA (22.2 g, 64.9 mmol) at room temperature. The mixture was heated at reflux (140° C.) for 1 hour before it was cooled to room temperature and decanted from the PPA. The solvent was evaporated under vacuum to obtain the crude product, which was purified by preparative HPLC to provide 1-(benzofuran-5-yl)cyclopropanecarboxylic acid (1.5 g, 5%). 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 7.95 (d, J=2.8 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.47 (d, J=11.6 Hz, 1H), 7.25 (dd, J=2.4, 11.2 Hz, 1H), 6.89 (d, J=1.6 Hz, 1H), 1.47-1.44 (m, 2H), 1.17-1.14 (m, 2H).

후처리

  1. additionwas added PPA (22.2 g, 64.9 mmol) at room temperature
  2. temperatureThe mixture was heated
  3. temperaturewas cooled to room temperature
  4. customdecanted from the PPA
  5. customThe solvent was evaporated under vacuum
  6. customto obtain the crude product, which
  7. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f0fcff4e740d42058315c46bc6b210a8
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

연결된 노트

불러오는 중…