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

HRID 401533

反応式

HRID 401533 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-05915495a9754168a0a540b07050c824
出典データセット
uspto-grants-2014_06
特許番号
US08741933B2

関連ノート

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