Sodium hydride → HCID 69650637, compound

HRID 1790885Notes

Reaction equation

HRID 1790885 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:13])[CH2:6]P(OC)(OC)=O.[CH3:14][C:15]1([C:20]2([CH:23]=O)[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17][O:16]1>C1COCC1>[CH3:3][O:4][C:5](=[O:13])/[CH:6]=[CH:23]/[C:20]1([C:15]2([CH3:14])[O:16][CH2:17][CH2:18][O:19]2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 143755571-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehyde

Product 1

HCID 69650637HCID 69650637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3 g of sodium hydride suspension (60% in paraffin oil) is introduced into 750 ml of THF, cooled under nitrogen to 0° C., and 10.9 g of dimethylphosphonoacetic acid methyl ester is added. Then, 7.5 g of aldehyde 7 is added in drops to 15 ml of THF, and it is stirred at room temperature for 2 hours. It is now quenched carefully with sodium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 9.5 g of title compound 93 accumulates as a colorless oil.

Workup

  1. customIt is now quenched carefully with sodium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium chloride solution
  4. customdried on sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 9.5 g of title compound 93 accumulates as a colorless oil

Sources & evidence

ORD record
ord-471da5d51b6b4cea9d594e1b3d56f24b
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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