Diethyl Oxalate → HCID 68358222, compound

HRID 1406000Notes

Reaction equation

HRID 1406000 reaction equation
[Li]N([Si](C)(C)C)[Si](C)(C)C.C1COCC1.[CH3:16][O:17][C:18]1([O:26][CH3:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=[O:25].[CH2:28]([O:30][C:31](=[O:37])[C:32](OCC)=[O:33])[CH3:29].OP([O-])(O)=O.[K+]>CCOCC>[CH3:27][O:26][C:18]1([O:17][CH3:16])[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([C:32](=[O:33])[C:31]([O:30][CH2:28][CH3:29])=[O:37])[C:19]1=[O:25]

Participants

7

Reactant 5

HCID 7268Diethyl OxalateHCID 8028TetrahydrofuranHCID 516951Monobasic potassium phosphateHCID 131671812,2-Dimethoxycycloheptan-1-oneHCID 178418261HCID 178418261, compound

Product 1

HCID 68358222HCID 68358222, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1M LiN(TMS)2 in THF (28.5 mL, 28.5 mmol) were added dropwise at −50° C. to a solution of 2,2-dimethoxycycloheptanone (4.10 g, 23.8 mmol) in 25 mL of Et2O under argon. After 30 minutes at the same temperature, 3.55 mL of diethyloxalate were also added under stirring. The solution was kept at room temperature overnight. 10% solution of KH2PO4 (20 mL) were then added and the resulting solution extracted with Et2O (3×50 mL). The organic layer was dried over Na2SO4 and evaporated to dryness. The crude was purified by chromatography on a silica gel column (eluant: AcOEt/cyclohexane 1/9) to afford 3.98 g (65% yield) as a colorless oil.

Workup

  1. extractionthe resulting solution extracted with Et2O (3×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude was purified by chromatography on a silica gel column (eluant: AcOEt/cyclohexane 1/9)
  5. customto afford 3.98 g (65% yield) as a colorless oil

Sources & evidence

ORD record
ord-88f058be812f4401b845c62790c489f8
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

Loading…