Tin tetrachloride → HCID 18182820, compound

HRID 1359241Notes

Reaction equation

HRID 1359241 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=4)[CH:11]=3)=[CH:7][C:6]=2[CH:22]=1.[C:23](Cl)(=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=4)[CH:11]=3)=[C:7]([C:23](=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27])[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 18182812HCID 18182812, compound

Product 1

HCID 18182820HCID 18182820, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the procedure described in Step 2 of Example 1, the title compound was prepared by the acylation of 5-chloro-2-(6-methoxy-naphth-2-yl)-1-benzofuran (6.6 g, 21.37 mmol), with valeryl chloride (2.3 mL, 16 mmol) in presence of tin (IV) chloride in chloroform. Purification by flash chromatography on silica gel using 2.5% ethyl acetate in hexane as the mobile phase yielded the title compound as a white solid (5.6 g), mp 119-120° C. Mass spectrum (+ESI, [M+NH4]+) m/z 410. 1HNMR (400 MHz, DMSO-d6): δ8.36 (d, 1H, J=1.6 Hz), 8.02 (dd, 2H, J=7.0, 2.2 Hz), 7.99 (s, 1H), 7.81 (dd, 1H, J=8.6, 1.7 Hz), 7.77 (d, 1H, J=8.8 Hz), 7.48-7.44 (m, 2H), 7.27 (dd, 1H, J=8.8, 2.3 Hz), 3.92 (s, 3H), 2.69 (t, 2H, J=7.3 Hz), 1.51 (m, 2H), 1.1 (m, 2H), and 0.68 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C24H21 ClO3: Calculated: C, 73.37; H, 5.39; N, 0.00. Found: C, 73.34; H, 5.27; N, 0.03.

Workup

  1. customPurification by flash chromatography on silica gel using 2.5% ethyl acetate in hexane as the mobile phase

Sources & evidence

ORD record
ord-d8c7145c473b4cc8b4b9e17416ca0b85
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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