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

HRID 1359204Notes

Reaction equation

HRID 1359204 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13]1[O:14][C:15]3[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=3[C:17]=1[C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:7]2.[H-].[Na+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[Br:1][C:2]1[C:3]2[C:8](=[CH:7][C:6]([C:13]3[O:14][C:15]4[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=4[C:17]=3[C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5][CH:4]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 113846851-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

Product 1

HCID 18182818Ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Method A, Step 5 of Example 1, the title compound was prepared from 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.58 g, 3.73 mmol), sodium hydride (0.194 g, 4.85 mmol), and ethyl bromoacetate (0.51 mL, 4.5 mmol) in DMF (15 mL). Purification by flash chromatography using 10% acetone in hexane as an eluant yielded a yellow gum (0.993 g); 1HNMR (200 MHz, DMSO-d6): δ8.5 (s, 1H), 8.25 (d, 1H, J=8.5 Hz), 8.15 (d, 1H, J=10 Hz), 7.95-8.1 (m, 2H), 7.75 (d, 1H, J=7.5 Hz), 7.2-7.4 (m, 3H), 5.15 (s, 2H), 4.15 (q, 2H, J=6.7 Hz), 2.75 (t, 2H, J=7.5 Hz), 1.5-1.65 (m, 2H), 1.1-1.3 (m, 4H), and 0.7 ppm (t, 3H, J=7.3 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-b5e0116288144b16974e6a3d24a960de
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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