Methyl iodide → HCID 68525850, 화합물

HRID 1036377

반응식

HRID 1036377 반응식
[O:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=O)[C:4]=2[CH:3]=[CH:2]1.[C:11](=[S:13])=S.IC.[H-].[Na+].[N+]([O-])(O)=O.[NH2:22][C:23]([NH2:25])=[NH:24].[O-][CH2:27]C.[Na+]>O1CCCC1.C(O)C.O>[CH3:27][S:13][C:11]1[C:8]2[CH2:7][CH2:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[C:9]=2[N:22]=[C:23]([NH2:25])[N:24]=1

참가 물질

10

반응물 6

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 10481Guanidine NitrateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-one

생성물 1

HCID 68525850HCID 68525850, 화합물

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 6,7-dihydro-4(5H)-benzofuranone (0.10 g, 0.73 mmol), carbon disulfide (0.048 mL, 0.80 mmol), and iodomethane (0.10 mL, 1.6 mmol) in tetrahydrofuran (1.8 mL) was treated with a 60% dispersion of sodium hydride in mineral oil (0.070 g, 1.8 mmol), stirred over night at ambient temperature and partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), filtered and concentrated. The residue was treated with guanidine nitrate (0.36 g, 2.9 mmol), treated with 1.46 mL (2.2 mol) of 1.5 M sodium ethoxide in ethanol, heated to 80° C. overnight, cooled, diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were dried (magnesium sulfate), filtered, concentrated and chromatographed using ethyl acetate in dichloromethane to provide the title compound: 1H NMR (300 MHz, CDCl3) δ 2.52 (s, 3H), 2.88-3.02 (m, 4H), 5.07 (br s, 2H), 6.87 (d, J=1.7 Hz, 1H), 7.37 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 234 (M+H)+.

후처리

  1. custompartitioned between saturated ammonium chloride and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureheated to 80° C. overnight
  7. temperaturecooled
  8. extractionextracted with dichloromethane (3×)
  9. dry with materialThe combined dichloromethane layers were dried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customchromatographed

출처 및 근거

ORD 기록
ord-526b7dac4178448484a28c1fd12e6619
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546410B2

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