Diflunisal → 1-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

HRID 1719725노트

반응식

HRID 1719725 반응식
[CH:1]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([F:14])=[CH:11][C:12]=2[F:13])=[CH:5][C:4]([C:15]([OH:17])=[O:16])=[C:3]([OH:18])[CH:2]=1.[H-].[Na+].[C:21](=[O:29])([O:25][CH:26](Cl)[CH3:27])[O:22][CH2:23][CH3:24]>CN(C=O)C>[F:13][C:12]1[CH:11]=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:6]1[CH:5]=[C:4]([C:15]([O:17][CH:23]([O:22][C:21]([O:25][CH2:26][CH3:27])=[O:29])[CH3:24])=[O:16])[C:3]([OH:18])=[CH:2][CH:1]=1

참가 물질

5

반응물 3

HCID 3059DiflunisalHCID 24758Sodium hydrideHCID 162095Carbonic acid, 1-chloroethyl ethyl ester

생성물 1

HCID 134913951-(Ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of diflunisal (5.0 g) in 40 ml DMF was added 0.8 g of sodium hydride (oil suspension containing 60% of NaH). The resultant mixture was stirred for 1.5 hours at room temperature before 3.0 ml of ethyl 1-chloroethyl carbonate was added dropwise. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The concentrate was partitioned between ether/ethyl acetate and acidified water. The organic layer was separated and the aqueous layer was extracted again with ether. The organic layers were combined, washed well with water, dried over anhydrous sodium sulfate and concentrated to 6.6 g of crude product. After further purification by chromatography (eluted through 120 g of silica gel with hexane, and then 5% ethyl acetate in hexane), the product was crystallized from hexane to afford 3.71 g of 1-(ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate.

후처리

  1. additionwas added dropwise
  2. concentrationconcentrated in vacuo
  3. customThe concentrate was partitioned between ether/ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted again with ether
  6. washwashed well with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to 6.6 g of crude product
  9. customAfter further purification by chromatography (
  10. washeluted through 120 g of silica gel with hexane
  11. custom5% ethyl acetate in hexane), the product was crystallized from hexane

출처 및 근거

ORD 기록
ord-f86c552ff4b14b5cbed0245ed8dd00c3
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04542158

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