Cesium carbonate → Ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate

HRID 1177268노트

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HRID 1177268 반응식
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([OH:17])[C:6]=2[CH:7]=1)[CH3:2].I[C:19]1[CH:29]=[CH:28][C:22]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1.[Cu]I>[CH3:26][N:25]([CH3:27])[C:23]([C:22]1[CH:28]=[CH:29][C:19]([O:17][C:8]2[C:6]3[CH:7]=[C:3]([CH2:1][CH3:2])[O:4][C:5]=3[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=2)=[CH:20][CH:21]=1)=[O:24]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 8799334-iodo-N,N-dimethylbenzamideHCID 59560005Ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate

생성물 1

HCID 59560279Ethyl 4-{4-[(dimethylamino)carbonyl]phenoxy}-2-ethyl-1-benzofuran-6-carboxylate수율 31.8%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1049Pyridine용매

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온도
100 °C

실험 절차

A mixture of ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate (0.8 g, 3.4 mmol), 4-iodo-N,N-dimethylbenzamide (0.9 g, 3.3 mmol), Cs2CO3 (1.12 g, 3.4 mmol) and CuI (400 mg, 2.1 mmol) in pyridine (30 mL) was heated to 100° C. for 24 hours. TLC (petroleum ether/EtOAc 4:1) indicated the complete consumption of the phenol. The solvent was removed under reduced pressure. The residue was poured into water (20 mL) and extracted with EtOAc (30 mL×2). The combined organic layers were washed with brine (20 mL×2), dried over Na2SO4 and concentrated. The product was purified via silica gel column chromatography using petroleum ether/EtOAc (20:1 to 1:1) to afford the desired compound (400 mg, 30%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (s, 1H), 7.56 (s, 1H), 7.43 (d, 2H), 7.00 (d, 2H), 6.27 (s, 1H), 4.44-4.35 (q, 2H), 3.15-3.04 (d, 6H), 2.83-2.78 (q, 2H), 1.45-1.37 (t, 3H), 1.37-1.26 (t, 3H).

후처리

  1. customthe complete consumption of the phenol
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was poured into water (20 mL)
  4. extractionextracted with EtOAc (30 mL×2)
  5. washThe combined organic layers were washed with brine (20 mL×2)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was purified via silica gel column chromatography

출처 및 근거

ORD 기록
ord-e8528040fdb047de84cf76d734204a9a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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