Diethyl Oxalate → HCID 67158314, compound

HRID 549243Notes

Reaction equation

HRID 549243 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[CH:7][C:8]([CH3:10])=O)[CH2:3][CH2:2]1.O1CCC(CC(C)=O)CC1.[C:21]([O:28][CH2:29][CH3:30])(=[O:27])[C:22](OCC)=O.CC(C)([O-])C.[Na+].[OH:37][CH2:38][CH2:39][NH:40][NH2:41]>C(O)C>[OH:37][CH2:38][CH2:39][N:40]1[C:8]([CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:10][C:22]([C:21]([O:28][CH2:29][CH3:30])=[O:27])=[N:41]1

Participants

7

Reactant 5

HCID 7268Diethyl OxalateHCID 80172-HydrazinoethanolHCID 217243441-(Oxan-4-yl)propan-2-oneHCID 229657531-(dihydro-2H-pyran-4(3H)-ylidene)propan-2-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 67158314HCID 67158314, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method described in Part B of Example 3 was repeated with 1-tetrahydro-4H-pyran-4-ylideneacetone (4.0 g, 28.5 mmol), and the resulting 1-tetrahydro-2H-pyran-4-ylacetone was mixed with diethyl oxalate (4.66 g, 31.9 mmol) and added to a solution of sodium tert-butoxide (3.07 g, 31.9 mmol) in ethanol (22 mL). The reaction was carried out according to the method described in Part C of Example 3 with the following modifications. Hydroxyethylhydrazine (2.43 g, 31.9 mmol) was used instead of ethylhydrazine oxalate. Extractions were carried out seven times with chloroform, and the crude product was not purified. Ethyl 1-(2-hydroxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylate (8.2 g) was obtained as a viscous yellow oil.

Workup

  1. extractionExtractions
  2. customthe crude product was not purified

Sources & evidence

ORD record
ord-09998cd0154548d485d2d132df3f9b04
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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