Hydrochloric Acid → 1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid

HRID 17917ノート

反応式

HRID 17917 の反応式
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=3[CH:18]=2)[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-].Cl>CO>[CH3:16][C:13]1([CH3:17])[C:12]2[CH:18]=[C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]3)[CH:9]=[CH:10][C:11]=2[O:15][CH2:14]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 591293551-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester

生成物 1

HCID 591295061-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid収率 41%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester (1 g, 4 mmol) in MeOH (10 mL) was added LiOH (0.40 g, 9.5 mmol). The mixture was stirred at 40° C. overnight. HCl (10%) was added slowly to adjust the pH to 5. The resulting mixture was extracted with ethyl acetate (10 mL×3). The extracts were washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by preparative HPLC to give 1-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid (0.37 g, 41%). 1H NMR (400 MHz, CDCl3) δ 7.11-7.07 (m, 2H), 6.71 (d, J=8 Hz, 1H), 4.23 (s, 2H), 1.66-1.63 (m, 2H), 1.32 (s, 6H), 1.26-1.23 (m, 2H).

後処理

  1. extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-88b2ef896de54098a663a08b95dfe47e
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

反応ノート

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