ChemicalBook CAS DataBase List METHYL 3-THIOPHENECARBOXYLATE 97

METHYL 3-THIOPHENECARBOXYLATE 97 synthesis

13synthesis methods

Product Name:METHYL 3-THIOPHENECARBOXYLATE 97
CAS Number:22913-26-4
Molecular formula:C6H6O2S
Molecular Weight:142.18

5,5-dimethyl-2-(thien-3-yl)-1,3,2-dioxaborinane

905966-46-3
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24424-99-5 Synthesis

24424-99-5
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74-88-4
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22913-26-4
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Yield: 58%

Reaction Conditions:

Stage #1:5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane;di-tert-butyl dicarbonate with 4,4'-dimethyl-2,2'-bipyridines;lithium methanolate;copper(l) chloride in N,N-dimethyl acetamide at 30; for 6 h;Inert atmosphere;Schlenk technique;
Stage #2:methyl iodide in N,N-dimethyl acetamide at 30; for 2 h;Schlenk technique;

Steps:

Methyl (Het)arylcarboxylates 3a-y, 5a-e; General Procedure
General procedure: A 15 mL Schlenk tube equipped with a stirrer bar was chargedwith CuCl (10 mol%), L7 (13 mol%), LiOMe (2.5 equiv), and theappropriate boronic ester 1 or 4 (0.375 mmol). The vessel wasthen evacuated and filled with Ar (three cycles). DMA (0.5 mL)and (Boc)2O (0.25 mmol) were added sequentially under Ar, andthe mixture was stirred at 30 for 6 h. MeI (5 equiv) was thenadded in air, and the mixture was stirred at 30 for additional2 h. The mixture was finally diluted with EtOAc and washedwith sat. aq NaCl (20 mL). The aqueous phase was furtherextracted with EtOAc (3 × 20 mL), and the combined organicphases were dried (Na2SO4) and concentrated. The residue waspurified by column chromatography [silica gel EtOAc-hexane(1:100 to 1:50)].

References:

Xu, Jin-Di;Su, Xiao-Bo;Wang, Cai;Yao, Li-Wei;Liu, Jing-Hui;Hu, Guo-Qin [Synlett,2021,vol. 32,# 8,art. no. ST-2020-U0651-L,p. 833 - 837] Location in patent:supporting information

67-56-1 Synthesis