Methanol → HCID 22613105, compound

HRID 844368Notes

Reaction equation

HRID 844368 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][C:16](=[O:22])[C:17]([O:19]CC)=[O:18])=[C:10]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C:9]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CO.[OH-].[Na+]>O>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][C:16](=[O:22])[C:17]([OH:19])=[O:18])=[C:10]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C:9]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22613182HCID 22613182, compound

Product 1

HCID 22613105HCID 22613105, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 200 mL round bottomed flask with a stirring bar and a nitrogen inlet was added ethyl 4-(benzyl-3-methoxy-2-methoxyethoxyphenyl)-2,4-dioxobutyrate (1.48 g, 3.57 mmol), THF (30 mL), methanol (30 mL), and sodium hydroxide solution (18 mL of a 1 N solution in water, 18 mmol). This mixture was stirred 2 h at ambient temperature. The organic solvents were removed in vacuo and the aqueous residue was diluted with 30 mL of water. This solution was washed with ethyl ether (2×50 mL) then acidified with 1N HCl. This mixture was extracted with ethyl ether (100 mL). The ether solution was washed with water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave a yellow oil. This material was crystallized by dissolving in 1:1 ether-hexane (−5mL) and storing in a freezer over night. The crystalline product was collected by filtration on a frit and dried in vacuo at ambient temperature to give 4-(benzyl-3-methoxy-2-methoxyethoxyphenyl)-2,4-dioxobutyric acid as yellow needles. MP: 83-85° C. Anal. Calc'd for C21H22O7: C, 65.28; H, 5.74; Found: C, 65.28; H, 6.05. 1H NMR (CDCl3): δ3.39 (s, 3H); 3.71 (t, j=4 Hz, 2H); 3.82 (s, 3H); 3.96 (s, 2H); 4.21 (t, j=4 Hz, 2H); 6.90 (d, j=2Hz, 1H); 7.28 (m, 6H); 9.60 (br s, 1H).

Workup

  1. customThe organic solvents were removed in vacuo
  2. additionthe aqueous residue was diluted with 30 mL of water
  3. washThis solution was washed with ethyl ether (2×50 mL)
  4. extractionThis mixture was extracted with ethyl ether (100 mL)
  5. washThe ether solution was washed with water and brine
  6. customDrying
  7. filtration(MgSO4), filtration and removal of the solvent in vacuo
  8. customgave a yellow oil
  9. customThis material was crystallized
  10. dissolutionby dissolving in 1:1 ether-hexane (−5mL) and storing in a freezer over night
  11. filtrationThe crystalline product was collected by filtration on a frit
  12. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-f7f79cc85777431ea214ed68156ea316
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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