Bromoacetonitrile → 2-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

HRID 1359199Notes

Reaction equation

HRID 1359199 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]#[N:32]>CN(C=O)C>[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]#[N:32])[CH:11]=[CH:10]2)(=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 113368791-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

Product 1

HCID 120828322-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

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-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (0.600 g, 1.74 mmol), sodium hydride (0.106 g, 2.65 mmol of a 60% dispersion on mineral oil) and bromoacetonitrile (0.18 mL, 2.6 mmol) in DMF (10 mL). Purification by flash chromatography using 60-80% chloroform in hexane as an eluant afforded a thick yellow oil (0.359 g). 1HNMR (200 MHz, DMSO-d6): δ8.45 (s, 1H), 8.0-8.2 (m, 3H), 7.85-7.95 (m, 1H), 7.7-7.8 (m, 1H), 7.65 (d, 1H, J=2.0 Hz), 7.35-7.5 (m, 1H), 5.35 (s, 2H), 2.75 (t, 2H, J=7.4 Hz), 1.45-1.65 (m, 2H), 1.05-1.25 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d727870964c84118960486d180f44196
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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