Methyl iodide → 6-Methoxy-2,3-dihydro-1-benzofuran-3-one

HRID 1865212노트

반응식

HRID 1865212 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:12][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2357176-Hydroxy-3-coumaranone

생성물 1

HCID 5853686-Methoxy-2,3-dihydro-1-benzofuran-3-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Hydroxybenzofuran-3(2H)-one (6 g, 40.0 mmol) was dissolved in DMF (80 mL), then added potassium carbonate (6.07 g, 43.97 mmol) and methyl iodide (4.12 mL, 65.95 mmol). The reaction was stirred at RT for 2 days. The mixture was filtered and the filtrate was concentrated in vacuo. The remaining oil was dissolved in EtOAc and washed with water. The aqueous layer was back-extracted with EtOAc (2×). The organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The remaining orange-red solid was purified by silica gel chromatography (1:4 EtOAc/hexane) to afford 6-methoxybenzofuran-3(2H)-one as a bright yellow crystalline solid. MS (ESI, pos. ion) m/z: 165.1 (M+1).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe remaining oil was dissolved in EtOAc
  4. washwashed with water
  5. extractionThe aqueous layer was back-extracted with EtOAc (2×)
  6. washThe organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe remaining orange-red solid was purified by silica gel chromatography (1:4 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-2af7ae6cb2b44065bc3bc974c7da1329
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626030B2

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