Hydrochloric Acid → Ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

HRID 1359197Notes

Reaction equation

HRID 1359197 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CN(C=O)C.O>[C:17]([C:16]1[C:15]2[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=2[O:13][C:12]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([O:1][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:11]=[CH:10]2)(=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 113368791-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

Product 1

HCID 12082831Ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled mixture of 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.01 g, 2.93 mmol) in DMF (10 mL) was added sodium hydride (0.21 g, 5.25 mmol of 60% dispersion on mineral oil). It was stirred for 50 minutes at room temperature then chilled in an ice bath. Ethyl bromoacetate (0.48 mL, 4.3 mmol) was added, and the reaction mixture was stirred at room temperature for one hour. The mixture was poured into excess water, acidified with 2N hydrochloric acid, and extracted with diethyl ether. The ethereal extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage apparatus) using 5-6% tert-butyl methyl ether in hexane as an eluant. The title compound was obtained as a yellow gum (0.749 g, 59%); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 7.9-8.1 (m, 3H), 7.8-7.9 (m, 1H, 7.7-7.8 (m, 1H), 7.3-7.5 (m, 4H), 4.95 (s, 2H), 4.2 (q, 2H, J=7.2 Hz), 2.7 (t, 2H, J=7.6 Hz), 1.45-1.65 (m, 2H), 1.0-1.3 (m, 5H), and 0.7 ppm (t, 3H, J=7.6 Hz).

Workup

  1. temperaturethen chilled in an ice bath
  2. stirringthe reaction mixture was stirred at room temperature for one hour
  3. extractionextracted with diethyl ether
  4. extractionThe ethereal extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-0327174798a24b0b8f443636f9dbb037
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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