Dimethyl Sulfate → Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

HRID 2177847노트

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HRID 2177847 반응식
O[C:2]1[C:12]([I:13])=[C:11]([OH:14])[CH:10]=[C:9]([CH3:15])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].COS([O:21][CH3:22])(=O)=O.[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:13][C:12]1[C:2]([O:21][CH3:22])=[C:3]([C:9]([CH3:15])=[CH:10][C:11]=1[O:14][CH3:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10519838Ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate2회

생성물 1

HCID 10915077Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate (Intermediate 204, 0.144 g), dimethylsulphate (0.085 ml) and potassium carbonate (0.185 g) in acetone (10 ml) was heated at reflux for 2.5 hours. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was partitioned between DCM and water and the organic layer was filtered through a phase separator. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate (0.158 g).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was partitioned between DCM and water
  7. filtrationthe organic layer was filtered through a phase separator
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

출처 및 근거

ORD 기록
ord-f6743098a12149aeab07f5b8dc351dcb
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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