Monoethyl malonate → HCID 90095309, compound

HRID 927268Notes

Reaction equation

HRID 927268 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([OH:5])=O.CCN(C(C)C)C(C)C.[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[C:26](=O)[O:25]C(=O)[CH2:23]2>C1COCC1.Cl>[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[C:26](=[O:25])[O:5][C:3]([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:23]2

Participants

6

Reactant 3

HCID 70615Monoethyl malonateHCID 81531DiisopropylethylamineHCID 217824866-Bromoisochroman-1,3-dione

Product 1

HCID 90095309HCID 90095309, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N,N′-Carbonyldiimidazole (747 mg, 4.61 mmol, 1.50 equiv.) was added to a stirred mixture of ethyl hydrogen malonate (0.543 mL, 4.61 mmol, 1.50 equiv.) in THF (15 mL) and the mixture was stirred at room temperature. After 15 min, Hunig's base (1.072 mL, 6.14 mmol, 2.00 equiv.) was added followed by dropwise addition of 6-bromoisochroman-1,3-dione (740 mg, 3.07 mmol) in THF (10 mL). Upon completion, the reaction was diluted with 0.5 N HCl (10 mL), extracted with EtOAc (2×20 mL), dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0-15% EtOAc/hexanes to give 683 mg of ethyl 2-(6-bromo-1-oxo-1H-isochromen-3-yl)acetate as a white solid.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-e8585207be6e4553a9601f88a3c5df62
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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