Diethyl Malonate → HCID 19032316, 화합물

HRID 266032노트

반응식

HRID 266032 반응식
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:13][C:14]1[CH:27]=[CH:26][C:25]2[C:24](=[O:28])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:29])[C:16]=2[CH:15]=1>C(O)C.C1COCC1>[CH3:13][C:14]1[CH:27]=[CH:26][C:25]2[C:24](=[O:28])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:29])[C:16]=2[C:15]=1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 2

HCID 7761Diethyl MalonateHCID 3444522-Bromomethyl-anthraquinone2회

생성물 1

HCID 19032316HCID 19032316, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Na metal (425 mg, 21.3 mmole) was dissolved in 50 mL of ethanol. To 5 mL of this solution, diethyl malonate (32 mg, 199 μmole) in 5 mL of THF was added, and the mixture was refluxed for 1 hour. 2-bromomethylanthraquinone (Compound 4.1) (50 mg, 166 μmole) in 5 mL of THF was then added to the refluxing reaction mixture. The reaction was refluxed for 8 hours, cooled to room temperature, and then quenched with 5 mL of saturated NH4Cl solution. The mixture was concentrated under vacuum, and redissolved in 20 mL of ethyl acetate for H2O extraction. The organic layer was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash silica column chromatography to yield 41 mg (54 %). 1H NMR (300 MHz, CDCl3) δ 8.11 (2H, m), 7.96 (1H, s), 7.88 (1H, d), 7.64 (1H, d), 7.37 (2H, m), 4.61 (2H, d), 4.20 (5H, m), 1.21 (6H, t).

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureThe reaction was refluxed for 8 hours
  3. customquenched with 5 mL of saturated NH4Cl solution
  4. concentrationThe mixture was concentrated under vacuum
  5. dissolutionredissolved in 20 mL of ethyl acetate for H2O extraction
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by flash silica column chromatography
  10. customto yield 41 mg (54 %)

출처 및 근거

ORD 기록
ord-87190998ba6244978d33de064d173bbc
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650399

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