反应 #1005977

ord-440eb576dccc4716a6192a3c366f500c

反应方程式

CC1(C)CC(=O)c2cc(C#C[Si](C)(C)C)ccc2S1
2,2-dimethyl-6-trimethylsilanylethynylthiochroman-4-one
O=C([O-])[O-].[K+].[K+]
K2CO3
C#Cc1ccc2c(c1)C(=O)CC(C)(C)S2
6-ethynyl-2,2-dimethylthiochroman-4-one
收率 99.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted with Et2O
  2. 2
    洗涤The combined organic layers were washed with H2O and saturated aqueous NaCl
  3. 3
    干燥dried over MgSO4
  4. 4
    其他Removal of the solvent under reduced pressure

实验过程

A solution of 2,2-dimethyl-6-trimethylsilanylethynylthiochroman-4-one (110.0 mg, 0.38 mmol) and K2CO3 (40.0 mg, 0.29 mmol) in 10.0 mL MeOH was stirred overnight at room temperature. The solution was diluted with H2O and extracted with Et2O. The combined organic layers were washed with H2O and saturated aqueous NaCl and dried over MgSO4. Removal of the solvent under reduced pressure afforded 81 mg (99%) of the 6-ethynyl-2,2-dimethylthiochroman-4-one as an orange oil. 1H NMR (300 MHz, CDCl3) δ: 8.20 (1H, d, J=1.9 Hz), 7.46 (1H, dd, J=1.9, 8.1 Hz), 7.18 (1H, d, J=8.1 Hz), 3.08 (1H, s), 2.86 (2H, s), 1.46 (6H, s).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09271946B2uspto-grants-2016_03