Acetic Acid → 2-(2-Ethynylphenyl)acetamide

A 1.0 M solution of TBAF in THF (59.1 mL, 59.1 mmol) was slowly added to a cooled (5° C. water/ice bath) solution of 2-(2-((trimethylsilyl)ethynyl)phenyl)acetamide (I7) (11.4 g, 49.3 mmol) in DCM (150 mL) and acetic acid (3.66 mL, 64.1 mmol). The mixture was stirred at 5° C. for 1 hour before 10% aqueous NaHCO3 solution (150 mL) was added. The resulting mixture was extracted with DCM (3×50 mL) then the combined organics were dried (MgSO4), filtered and evaporated in vacuo until approximately 15 mL of solvent remained. This solution was diluted with Et2O (100 mL) and EtOAc (100 mL) resulting in the formation of a precipitate, which was filtered and dried to give 2.81 g of the title compound I8 as a brown solid. The remaining filtrate was adsorbed onto silica gel and purified using column chromatography (CombiFlash Rf, 80 g SiO2 Cartridge, 0-10% MeOH in DCM). An additional 2.62 g of the title compound I8 was isolated as a brown solid (combined total 5.43 g, 69%); 1H NMR (300 MHz, d6-DMSO) δ 7.44 (d, J=7.5 Hz, 1H), 7.21-7.37 (m, 4H), 6.93 (brs, 1H), 4.32 (s, 1H), 3.59 (s, 2H). LCMS-B: rt 4.734 min; m/z 160 [M+H]+.

1. additionwas added
2. extractionThe resulting mixture was extracted with DCM (3×50 mL)
3. dry with materialthe combined organics were dried (MgSO4)
4. filtrationfiltered
5. customevaporated in vacuo until approximately 15 mL of solvent
6. additionThis solution was diluted with Et2O (100 mL) and EtOAc (100 mL)
7. customresulting in the formation of a precipitate, which
8. filtrationwas filtered
9. customdried

ORDレコード

ord-f567f3867bb14708b9cd48b3fd1a95db

出典データセット

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09266864B2