Triethylamine → 7-Methoxybenzofuran-3-yl trifluoromethanesulfonate

HRID 1057145

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HRID 1057145 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 208271337-Methoxybenzofuran-3-yl trifluoromethanesulfonate수율 71.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d20252678344c9caa96707f7986cd18
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

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