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

HRID 1643741Notes

Reaction equation

HRID 1643741 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-059b22b447d44ba3aa3cdc0ec93dc56b
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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