Diethyl Oxalate → HCID 12677785, compound

HRID 2419475Notes

Reaction equation

HRID 2419475 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)[S:6][CH2:5]1)(=[O:3])[CH3:2].[C:15](OCC)(=O)[C:16]([O:18]CC)=[O:17].[H-].[Na+]>O1CCCC1>[O:3]=[C:1]1[CH:2]=[C:15]([C:16]([OH:18])=[O:17])[O:14][C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[S:6][CH2:5][C:4]1=2

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 12677769HCID 12677769, compound

Product 1

HCID 12677785HCID 12677785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 3-acetyl-4-thiochromanone (6.18 g, 0.03 mole, described in Example 5) and diethyl oxalate (4.38 g, 0.03 mole) in tetrahydrofuran (25 ml) is added dropwise to a stirred suspension of 57% sodium hydride (3.79 g, 0.09 mole) in tetrahydrofuran (25ml) under an atmosphere of nitrogen at 70°. After the addition is completed, the mixture is heated under an atmosphere of nitrogen at 70° C for 17 hr and the solvent removed by evaporation under reduced pressure. The residue is dissolved in water and washed with ether. The aqueous phase is acidified with concentrated hydrochloric acid (15 ml) in the presence of chloroform and the mixture is stirred for 1.5 hr. at room temperature. The organic phase is separated and the aqueous phase is extracted with chloroform. The combined organic extracts are dried, evaporated and the resulting residue crystallized from chloroform to give the title compound; m.p. 251°-253° C, νmaxnujol 2500, 1890, 1730, 1640, 1575, 1550 and 1265 cm-1.

Workup

  1. additionAfter the addition
  2. customthe solvent removed by evaporation under reduced pressure
  3. dissolutionThe residue is dissolved in water
  4. washwashed with ether
  5. customat room temperature
  6. customThe organic phase is separated
  7. extractionthe aqueous phase is extracted with chloroform
  8. customThe combined organic extracts are dried
  9. customevaporated
  10. customthe resulting residue crystallized from chloroform

Sources & evidence

ORD record
ord-f7e89891ac8c4e1a98cc001078fad4c1
Source dataset
uspto-grants-1978_08
Patent number
US04105778

Reaction notes

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