2,2-Dimethyl-1,3-dioxane-4,6-dione → 2,2-DiMethyl-5-[(2,4,5-trifluorophenyl)acetyl]-1,3-dioxane-4,6-dione

HRID 221421

반응식

HRID 221421 반응식
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=1[CH2:20][C:21](O)=[O:22].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]([C:21](=[O:22])[CH2:20][C:13]2[CH:14]=[C:15]([F:19])[C:16]([F:18])=[CH:17][C:12]=2[F:11])[C:4](=[O:9])[O:3]1

참가 물질

6

반응물 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779502,4,5-Trifluorophenylacetic acid

생성물 1

HCID 497840752,2-DiMethyl-5-[(2,4,5-trifluorophenyl)acetyl]-1,3-dioxane-4,6-dione수율 96%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

2,2-Dimethyl-[1,3]dioxane-4,6-dione (5.69 g, 39.5 mmol) was dissolved in 400 mL of dichloromethane under stirring, followed by addition of (2,4,5-trifluorophenyl)-acetic acid 1a (7.15 g, 37.6 mmol) and 4-dimethylaminopyridine (7.35 g, 60.2 mmol) in an ice-water bath. Then a suspension of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.28 g, 43.2 mmol) in 250 mL of dichloromethane was added dropwise slowly. After stirring at room temperature for 36 hours, the reaction mixture was washed with the solution of 5% potassium bisulfate (250 mL×7) and saturated brine (250 mL×2), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2,2-dimethyl-5-[2-(2,4,5-trifluoro-phenyl)-acetyl]-[1,3]dioxane-4,6-dione 1b (11.4 g, yield 96%) as a white solid.

후처리

  1. additionwas added dropwise slowly
  2. stirringAfter stirring at room temperature for 36 hours
  3. washthe reaction mixture was washed with the solution of 5% potassium bisulfate (250 mL×7) and saturated brine (250 mL×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-95593b41e190407bbe52c20bfa2f8c4d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207161B2

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