Diethyl Oxalate → HCID 12677754, compound

HRID 2419471Notes

Reaction equation

HRID 2419471 reaction equation
[C:1]([CH:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[C:17](OCC)(=[O:23])[C:18]([O:20]CC)=[O:19]>O1CCCC1>[O:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[CH:4]([C:1](=[O:3])[CH2:2][C:17](=[O:23])[C:18]([OH:20])=[O:19])[CH2:5]1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 12677753HCID 12677753, compound

Product 1

HCID 12677754HCID 12677754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Solid 3-acetyl-4-chromanone (0.570 g, 3 mmoles, described in Example 5) is added in portions at room temperature to a suspension of 57% sodium hydride (0.379 g, 9 mmoles) in dry tetrahydrofuran (10 ml). The mixture is heated within 15 min to 60° C and diethyl oxalate (0.438 g, 3 mmoles) in tetrahydrofuran (10 ml) is added. After heating at reflux temperature under an atmosphere of nitrogen for 17 hr., the solvent is removed under reduced pressure, the residue is dissolved in ice-water and extracted with ether. The aqueous phase is acidified with 6N hydrochloric acid and extracted with chloroform. The organic phase is dried, evaporated, and the residue crystallized from methanol-chloroform to give 4-(4-chromanone-3-yl)-2,4-dioxobutyric acid (Vl; R1, R2, R3, Rl4 and R5 = H, and X = O), νmaxnujol 1705, 1615 and 1560 cm-1.

Workup

  1. additionis added
  2. temperatureAfter heating
  3. temperatureat reflux temperature under an atmosphere of nitrogen for 17 hr
  4. custom, the solvent is removed under reduced pressure
  5. dissolutionthe residue is dissolved in ice-water
  6. extractionextracted with ether
  7. extractionextracted with chloroform
  8. customThe organic phase is dried
  9. customevaporated
  10. customthe residue crystallized from methanol-chloroform

Sources & evidence

ORD record
ord-f378fd51dcae4b1c9b234778b5d2010c
Source dataset
uspto-grants-1978_08
Patent number
US04105778

Reaction notes

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