Diethyl Oxalate → HCID 12677785, compound
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=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 (25 ml) 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
- additionAfter the addition
- customthe solvent removed by evaporation under reduced pressure
- dissolutionThe residue is dissolved in water
- washwashed with ether
- customThe organic phase is separated
- extractionthe aqueous phase is extracted with chloroform
- customThe combined organic extracts are dried
- customevaporated
- customthe resulting residue crystallized from chloroform
Sources & evidence
- ORD record
- ord-ebb9ebbdcfcd4739b1f883f58bddbbd8
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060619
Reaction notes
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