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

HRID 1177076노트

반응식

HRID 1177076 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a85bd5a792a84fa186f863e077f2c75c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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