Trifluoromethanesulfonic acid → 5-Methanesulfonyl-3,3-dimethyl-2,3-dihydro-benzofuran

HRID 460305노트

반응식

HRID 460305 반응식
[CH3:1][C:2]1([CH3:11])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.F[C:13](F)(F)[S:14](O)(=[O:16])=[O:15].CS(OS(C)(=O)=O)(=O)=O>>[CH3:13][S:14]([C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:3][C:2]([CH3:11])([CH3:1])[C:6]=2[CH:7]=1)(=[O:16])=[O:15]

참가 물질

4

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 81560Methanesulfonic anhydrideHCID 111593943,3-Dimethyl-2,3-dihydro-1-benzofuran

생성물 1

HCID 184454195-Methanesulfonyl-3,3-dimethyl-2,3-dihydro-benzofuran수율 119.7%

반응 조건

온도
135 °C

실험 절차

A mixture of 3,3-dimethyl-2,3-dihydro-benzofuran (example 14c) (870 mg, 5.87 mmol), trifluoromethanesulfonic acid (0.1 mL, 1.17 mmol) and methanesulfonic anhydride (2.04 g, 11.74 mmol) was heated to 135° C. After reaching this temperature, the heater was removed and the mixture was cooled down to room temperature. The mixture was poured into a solution of ice-water. The aqueous layer was extracted twice with ethyl acetate and the organic combined extract was washed with water, an aqueous solution of sodium bicarbonate, brine, dried (MgSO4), filtered, and evaporated. The residue was chromatographed on silica gel (30% to 50% ethyl acetate in hexane) to afford 317 mg of 5-Methanesulfonyl-3,3-dimethyl-2,3-dihydro-benzofuran. 24% yield. 1H-NMR (300 MHz, CDCl3): 1.39 (s, 6H), 3.04 (s, 3H), 4.36 (s, 2H), 6.90 (d, J=8.2 Hz, 1H), 7.67 (d, J=2.1 Hz, 1H), 7.74 (dd, J1=8.5 Hz, J2=2.1 Hz, 1H).

후처리

  1. customthe heater was removed
  2. temperaturethe mixture was cooled down to room temperature
  3. additionThe mixture was poured into a solution of ice-water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. extractionthe organic combined extract
  6. washwas washed with water
  7. dry with materialan aqueous solution of sodium bicarbonate, brine, dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was chromatographed on silica gel (30% to 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8307b2abfb8c4e739c66c8a9f79813a8
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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