Methyl Ethyl Ketone → Ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate

HRID 2107101노트

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HRID 2107101 반응식
[C:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([O:16][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1784395372-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine

생성물 1

HCID 14053136Ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate수율 78.7%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

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온도
60 °C

실험 절차

To a mixture of 0.06 g of 2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine obtained in Example 14, 0.06 g of ethyl bromoacetate, 0.04 g of anhydrous potassium carbonate and 3 ml of methyl ethyl ketone was added a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred at 60° C. for 1 hour. Water was added to the reaction mixture The resultant mixture was extracted with ethyl acetate After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (6:1) gave 0.06 g of ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate.

후처리

  1. extractionwas extracted with ethyl acetate After the extract
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off The residue
  4. washElution
  5. additionwith a mixture of hexane-ethyl acetate (6:1)

출처 및 근거

ORD 기록
ord-7dd4ad97a72647cdafd9b060d3301cba
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04933348

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