Tin tetrachloride → 1-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359207Notes

Reaction equation

HRID 1359207 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=1[C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 66054Isovaleryl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

Product 1

HCID 181827841-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), was acylated with isovaleryl chloride (1.9 mL, 16 mmol), in presence of tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant then by using the Biotage apparatus using 1.5% ethyl acetate in hexane as an eluant yielded the title compound as a yellow wax (1.34 g); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (d, 3H, J=8.2 Hz), 7.8 (d, 1H, J=10.2 Hz), 7.7 (d, 1H, J=7.7 Hz), 7.35-7.55 (m, 3H), 7.3 (d, 1H, J=8.7 Hz), 3.95 (s, 3H), 2.6 (d, 2H, J=7.7 Hz), 2.0-2.1 (m, 1H), and 0.75 ppm (d, 6H, J=7.7 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-142eea6ab14b40a787bbe2db0bd48c25
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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