Diethyl Malonate → HCID 19032316, compound

HRID 266032Notes

Reaction equation

HRID 266032 reaction equation
[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]

Participants

5

Reactant 2

HCID 7761Diethyl MalonateHCID 3444522-Bromomethyl-anthraquinone2×

Product 1

HCID 19032316HCID 19032316, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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 %)

Sources & evidence

ORD record
ord-87190998ba6244978d33de064d173bbc
Source dataset
uspto-grants-1997_07
Patent number
US05650399

Reaction notes

Loading…