Dimethyl Sulfide → Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

HRID 2217368노트

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HRID 2217368 반응식
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[C:5]=1[CH2:14][CH:15]=C.[O:18]=[O+][O-].CSC>ClCCl.CO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]2[O:13][CH:15]([OH:18])[CH2:14][C:5]=12)=[O:17]

참가 물질

6

반응물 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 59768300Methyl 2-allyl-3-hydroxy-4-nitro-benzoate

생성물 1

HCID 20738652Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
-70 °C

실험 절차

Into a solution of 2-allyl-3-hydroxy-4-nitro-benzoic acid methyl ester (6.11 g 25.6 mmol) in dichloromethane (100 mL) and methanol (10 mL) at −78° C. was bubbled with ozone for 40 minutes. After stirring for another 20 min at −70° C., a stream of nitrogen gas was passed through the reaction mixture. Dimethyl sulfide (5 mL, 68.1 mmol) was added at −78° C. The reaction solution was allowed to warm up gradually to room temperature overnight. The reaction mixture was partitioned between dichloromethane and water. The aqueous layer was further extracted twice with dichloromethane. The organic extract was washed with brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure to give 2-hydroxy-7-nitro-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester as a yellow solid (6.0 g). 1H NMR (CDCl3) &: 3.51-3.74 (m, 2H), 3.96 (s, 3H), 6.43 (dd, 1H, J=6.4 Hz, 2.6 Hz), 7.63 (d, 0.1H, J=8.8), 8.01 (d, 1H, J=8.9 Hz).

후처리

  1. temperatureto warm up gradually to room temperature overnight
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. extractionThe aqueous layer was further extracted twice with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cd55034c19c44150a84f0bfd90f5ec0c
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407980B2

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