Water → HCID 86680191, compound

HRID 2402343Notes

Reaction equation

HRID 2402343 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:19]1([CH:23]=O)[CH2:22][CH2:21][CH2:20]1.O>C1COCC1.CN(C=O)C>[CH:19]1(/[CH:23]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 12431621Cyclobutanecarbaldehyde

Product 1

HCID 86680191HCID 86680191, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

6.4 ml (27.3 mmol) of tert-butyl (diethoxyphosphoryl)acetate were added dropwise to a suspension, cooled to 0° C., of 1.05 g (60% in mineral oil, 26.2 mmol) of sodium hydride in a mixture of 22 ml of THF and 22 ml of DMF. After 30 min, the mixture was cooled to −10° C., and 2.0 g (crude, about 23.8 mmol) of cyclobutanecarbaldehyde were added in several portions. The reaction mixture was stirred at 0° C. for 5 h and then slowly warmed to RT overnight, subsequently added to water and extracted three times with ethyl acetate. The organic phases were combined and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1). This gave 1.21 g of the target product (about 28% of theory).

Workup

  1. temperatureslowly warmed to RT overnight
  2. extractionextracted three times with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-23cc37b04c7e4462a041029c25a629d3
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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