Ethyl 4-hydroxybenzofuran-6-carboxylate → Ethyl 4-hydroxy-2,3-dihydrobenzofuran-6-carboxylate

HRID 1177078ノート

反応式

HRID 1177078 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]([OH:15])[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]([OH:15])[C:9]2[CH2:10][CH2:11][O:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

参加物

4

反応物 1

HCID 11344757Ethyl 4-hydroxybenzofuran-6-carboxylate

生成物 1

HCID 59559879Ethyl 4-hydroxy-2,3-dihydrobenzofuran-6-carboxylate収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

Pd on carbon (100 mg) was added to a solution of 4-hydroxy-benzofuran-6-carboxylic acid ethyl ester (8a) (333 mg, 1.61 mmol) in acetic acid. The mixture was stirred under H2 (50 psi) for 48 hr. The mixture was filtered through Celite and concentrated. The residue was taken into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 15% EtOAc in hexanes to give a pale yellow solid (315 mg, 94% yield). 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J=1.26 Hz, 1 H) 7.05 (s, 1 H) 4.65 (t, J=8.72 Hz, 2 H) 4.35 (q, J=7.07 Hz, 2 H) 3.21 (t, J=8.72 Hz, 2 H) 1.38 (t, J=7.07 Hz, 3 H); LCMS for C11H12O4 m/z 209.10 (M+H)+.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 15% EtOAc in hexanes

出典と根拠

ORDレコード
ord-a317aeeb32274811add9ef41c1672ec2
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

反応ノート

読み込み中…