Acetic Acid → Methyl 6-hydroxy-2,3-dihydrobenzofuran-4-carboxylate

HRID 1643549ノート

反応式

HRID 1643549 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:14])[CH:8]=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=[O:4].C(O)(=O)C>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:14])[CH:8]=[C:9]2[O:13][CH2:12][CH2:11][C:10]=12)=[O:4]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 595601586-Hydroxy-benzofuran-4-carboxylic acid methyl ester

生成物 1

HCID 59559984Methyl 6-hydroxy-2,3-dihydrobenzofuran-4-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-hydroxy-benzofuran-4-carboxylic acid methyl ester (6d) (354 mg, 1.82 mmol) in EtOAc was added acetic acid (1 mL) and Pd on carbon (40 mg). The reaction mixture was stirred under hydrogen gas balloon overnight. The mixture was filtered through Celite and concentrated to give a pale yellow solid which was used without further purification. LCMS and NMR showed it was a mixture of 6-hydroxy-benzofuran-4-carboxylic acid methyl ester and 6-hydroxy-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (2:1). 1H NMR (400 MHz, CDCl3) δ 7.02 (d, J=2.27 Hz, 2 H) 6.53 (d, J=2.27 Hz, 1 H) 4.61 (t, J=8.72 Hz, 2 H) 3.90 (s, 3 H) 3.44 (t, J=8.72 Hz, 2 H).

後処理

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give a pale yellow solid which
  4. customwas used without further purification
  5. additiona mixture of 6-hydroxy-benzofuran-4-carboxylic acid methyl ester and 6-hydroxy-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (2:1)

出典と根拠

ORDレコード
ord-c84db56c0ac4421d91111873f75cd3a6
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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