تفاعل #1005977

ord-440eb576dccc4716a6192a3c366f500c

معادلة التفاعل

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
المردود 99.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصextracted with Et2O
  2. 2
    غسيلThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. 3
    تجفيفdried over MgSO4
  4. 4
    أخرىRemoval of the solvent under reduced pressure

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09271946B2uspto-grants-2016_03