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

HRID 17924

反応式

HRID 17924 の反応式
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

参加物

3

反応物 1

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

生成物 1

HCID 513584541-(Benzofuran-5-yl)cyclopropanecarboxylic acid収率 11.4%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
140 °C

実験手順

To a suspension of crude 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).

後処理

  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

出典と根拠

ORDレコード
ord-801490dfe0a14cc0b21adbde6954e499
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

関連ノート

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