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Triethyl phosphonoacetate → HCID 59585994, 화합물

HRID 1399120
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HRID 1399120 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[C:30]2=[N:31][C:32]3[C:33](=[C:34]([CH:38]=O)[CH:35]=[CH:36][CH:37]=3)[N:29]2[CH2:28][CH2:27][CH2:26]1>O1CCCC1.O>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[C:30]2=[N:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34](/[CH:38]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:33]=3[N:29]2[CH2:28][CH2:27][CH2:26]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 57786099HCID 57786099, 화합물

생성물 1

HCID 59585994HCID 59585994, 화합물수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Sodium hydride (60% in oil, 230 mg, 5.76 mmol) was added to a stirred solution of ethyl (diethoxyphosphoryl)acetate (1.94 g, 8.67 mmol) in tetrahydrofuran (14 mL) at 0° C. After stirring 10 min, 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (1.00 g, 2.88 mmol) in tetrahydrofuran (1.0 mL) was added to the mixture, and the mixture was stirred at room temperature for 12 hr. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with diisopropyl ether to give the title compound as a colorless powder (908 mg, 2.18 mmol, 76%).

후처리

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-8e5375a78bd9431cb62bb1bcb07c7268
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901141B2

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