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ChemicalBook CAS DataBase List N-(4-ethynylphenyl)acetamide
35447-83-7

N-(4-ethynylphenyl)acetamide synthesis

12synthesis methods
-

Yield:35447-83-7 98%

Reaction Conditions:

with potassium fluoride in lithium hydroxide monohydrate;N,N-dimethyl-formamide at 20; for 0.5 h;

Steps:

Synthesis of N-(4-ethynylphenyl)acetamide (1j)

N-(4-(2-(trimethylsilyl)ethynyl)phenyl)acetamide (870 mg, 3.8 mmol) , KF (359 mg, 6.2 mmol), DMF (40 mL), and H2O (4 mL) were stirred at rt. After complete conversion of the starting materials as monitored by TLC (eluent: petroleum ether/ethyl acetate =1/1), water (10 mL) was added, the organic layer was separated. The aqueous phase was extracted with ethyl acetate (10 mL × 3), the organic phase was combined and washed with a saturated aqueous solution of NaCl, and dried over anhydrous MgSO4. The solvent was evaporated. Flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 3/1→2/1→1/1) afforded 1j as a pale yellow solid (592 mg, 98%).

References:

Xu, Cai-Xia;Ma, Cun-Hua;Xiao, Fu-Rong;Chen, Hong-Wei;Dai, Bin [Chinese Chemical Letters,2016,vol. 27,# 11,p. 1683 - 1685] Location in patent:supporting information