Dimethyl Sulfate → Methyl 4-acetamido-3-allyl-5-chloro-2-methoxybenzoate

HRID 2074000ノート

反応式

HRID 2074000 の反応式
[CH2:1]([C:4]1[C:5]([OH:19])=[C:6]([CH:11]=[C:12]([Cl:18])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].[H-].[Na+].S(OC)(O[CH3:26])(=O)=O>CN(C=O)C>[CH2:1]([C:4]1[C:5]([O:19][CH3:26])=[C:6]([CH:11]=[C:12]([Cl:18])[C:13]=1[NH:14][C:15](=[O:17])[CH3:16])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 14883225Methyl 4-acetamido-3-allyl-5-chloro-2-hydroxybenzoate

生成物 1

HCID 10709158Methyl 4-acetamido-3-allyl-5-chloro-2-methoxybenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the phenolic compound of step 6 above (4 g) and NaH (0.7 g) in DMF (50 ml) is stirred for 15 minutes. Dimethyl sulfate (2 g) is added and the mixture is stirred for 16 hours. The mixture is partitioned between CH2Cl2 and H2O, and the organic layer is separated and washed with H2O, dried (MgSO4) and evaporated. The solid residue is twice recrystallized from MeOH-H2O and chromatographed on silica gel affording the desired product which is used in the next step.

後処理

  1. stirringthe mixture is stirred for 16 hours
  2. customThe mixture is partitioned between CH2Cl2 and H2O
  3. customthe organic layer is separated
  4. washwashed with H2O
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe solid residue is twice recrystallized from MeOH-H2O
  8. customchromatographed on silica gel affording the desired product which

出典と根拠

ORDレコード
ord-21d8aa6f872545a09adbca85d2bb5350
出典データセット
uspto-grants-1990_04
特許番号
US04920219

反応ノート

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