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

HRID 1177078노트

반응식

HRID 1177078 반응식
[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]

참가 물질

4

반응물 1

HCID 11344757Ethyl 4-hydroxybenzofuran-6-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a317aeeb32274811add9ef41c1672ec2
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

반응 노트

불러오는 중…