Ammonium Chloride → Bis(2-methyl-4-thienyl)methane

温度

-65 °C

31.3 g of 2-methyl-4-bromo-thiophene (0.177 mol) was dissolved in 150 ml ether and treated dropwise with 113 ml 1.6M BuLi (0.1 mol) at −70° C. The resulting solution kept under stirring at −60 to −70° C. for 30 min and then was treated with 22.3 g 2-methyl-4-thiophene-aldehyd (0.177 mol) in 100 ml ether. The mixture was allowed to warm to r.t., then neutralized by 10% aq. NH4Cl and washed with water. The organic phase was collected and evaporated off. The suspension of 10 g LiAlH4 (0.266 mol) in 100 ml ether was treated dropwise with the solution of 35.5 g AlCl3 (0.266 mol) in 100 ml ether. The resulting mixture was treated with the solution of the compound obtained in the previous reaction in 100 ml ether. The mixture refluxed for additional 1 h, cooled up to r.t. and treated with 100 ml ethyl acetic ester. Then the mixture was treated with 300 ml H2O and 300 ml ether. Organic phase was collected, washed with water, dried over MgSO4 and evaporated off. The residue was distilled at 90-110/0.5 mmHg. Yield 23.2 g (63%). The title compound was analyzed by 1H-NMR spectroscopy.

1. temperatureto warm to r.t.
2. washwashed with water
3. customThe organic phase was collected
4. customevaporated off
5. additionThe resulting mixture was treated with the solution of the compound
6. temperatureThe mixture refluxed for additional 1 h
7. temperaturecooled up to r.t.
8. customOrganic phase was collected
9. washwashed with water
10. dry with materialdried over MgSO4
11. customevaporated off
12. distillationThe residue was distilled at 90-110/0.5 mmHg

ORDレコード

ord-a0b080779b714050a9a08d47d0847535

出典データセット

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06822106B2