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

HRID 2074000노트

반응식

HRID 2074000 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-21d8aa6f872545a09adbca85d2bb5350
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04920219

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