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

HRID 2177847ノート

反応式

HRID 2177847 の反応式
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]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10519838Ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-f6743098a12149aeab07f5b8dc351dcb
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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