Triethylamine → 7-Methoxybenzofuran-3-yl trifluoromethanesulfonate

HRID 1057145

反応式

HRID 1057145 の反応式
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]1[C:26]2[O:25][CH2:24][C:23](=O)[C:22]=2[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:23]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:17][CH3:16])[C:26]=2[O:25][CH:24]=1)(=[O:5])=[O:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 28181127-Methoxybenzofuran-3(2H)-one

生成物 1

HCID 208271337-Methoxybenzofuran-3-yl trifluoromethanesulfonate収率 71.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

Trifluoromethanesulfonic anhydride (4.6 g, 16.3 mmol) was added dropwise to a solution of 7-methoxybenzofuran-3(2H)-one (1.8 g, 10.9 mmol), triethylamine (2.2 g, 21.8 mmol), and dichloromethane (40 mL) at −20° C. The resulting mixture was stirred at −20° C. for 2 h. The reaction mixture was neutralized with saturated aqueous NaHCO3 (22 mL). The organic layer was separated, washed with water (40 mL) and brine (40 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column using petroleum ether to afford the title compound as yellow oil (2.3 g, yield 71%). 1H NMR (DMSO-d6, 400 MHz): δ 8.67 (s, 1H), 7.36 (t, 1H), 7.21 (d, 1H), 7.20 (d, 1H), 3.96 (s, 3H).

後処理

  1. customThe organic layer was separated
  2. washwashed with water (40 mL) and brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column

出典と根拠

ORDレコード
ord-4d20252678344c9caa96707f7986cd18
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

関連ノート

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