Tin tetrachloride → (2-Ethyl-benzofuran-3-yl)-(2'-methoxy-[1,1';3',1"]terphenyl-5'-yl)-methanone

HRID 1067319Notes

Reaction equation

HRID 1067319 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([C:15](O)=[O:16])=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)(=O)C(Cl)=O.[CH2:30]([C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[CH:36]=1)[CH3:31].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH2:30]([C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[C:36]=1[C:15]([C:6]1[CH:7]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]([O:2][CH3:1])=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=1)=[O:16])[CH3:31]

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 765822-EthylbenzofuranHCID 234456322'-Methoxy-[1,1';3',1"]terphenyl-5'-carboxylic acid

Product 1

HCID 23445613(2-Ethyl-benzofuran-3-yl)-(2'-methoxy-[1,1';3',1"]terphenyl-5'-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 2′-methoxy-[1,1′;3′,1″]terphenyl-5′-carboxylic acid (1.031 g, 3.388 mmol), oxalyl chloride (0.325 mL, 3.727 mmol), commercial 2-ethylbenzofuran (0.4953 g, 3.388 mmol) and tin (IV) chloride (0.436 mL, 3.727 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 3% EtOAc/ pet. ether gave 1.070 g, (73%) of the tide compound. 1H NMR (DMSO-d6) δ1.24 (t, 3H), 2.90 (quartet, 2H), 3.21 (s, 3H), 7.30-7.67 (m, 14H), 7.75 (s, 2H).

Workup

  1. customPurification on Biotage KP-Sil
  2. washeluting with 3% EtOAc/ pet. ether

Sources & evidence

ORD record
ord-f0383a3b630c4071a51cc840427b4b3c
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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