Tin tetrachloride → Ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

HRID 1359232Notes

Reaction equation

HRID 1359232 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([Cl:20])=[C:15]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=[CH:13]2.[C:28](Cl)(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:20][C:16]1[C:17]2[C:12](=[CH:11][C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]=3[C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 18182814HCID 18182814, compound

Product 1

HCID 18182776Ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetateYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described in Step 3 of Example 23, ethyl 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetate (1.90 g, 4.99 mmol) was acylated by valeryl chloride (0.61 mL, 5.1 mmol) in presence of tin (IV) chloride (0.60 mL, 5.1 mmol) in methylene chloride (20 mL). ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy} acetate was prepared. Purification by HPLC using 10% tert-butyl methyl ether in hexane as the mobile phase yielded the title compound as a light yellow solid (0.533 g), mp 95-97° C. Mass spectrum (+ESI, [M+H]+) m/z 465. 1HNMR (500 MHz, DMSO-d6): δ8.5 (s, 1H), 8.25 (d, 1H, J=8.9 Hz), 8.15 (d, 1H, J=9.0 Hz), 8.05 (t, 2H, J=8.6 Hz), 7.75 (d, 1H, J=7.8 Hz), 7.55 (d, 1H, J=9.2 Hz), 7.4-7.45 (m, 2H), 5.13 (s, 2H), 4.2 (q, 2H, J=7.0 Hz), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.3 (m, 5H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C27H25ClO5: Calculated: C, 69.75; H, 5.42; N, 0.00. Found: C, 69.64; H, 5.20; N, 0.01.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-b442c3c3cb6c41a68e942cdef9bf4afe
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…