Methyl iodide → HCID 12425357, compound

HRID 610467Notes

Reaction equation

HRID 610467 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:17]([Li])CCC.IC>C1COCC1>[O:4]=[C:3]([CH2:5][CH3:17])[CH2:2][C:1]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 142266Benzyl acetoacetateHCID 178418339Butyllithium

Product 1

HCID 12425357HCID 12425357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the procedure of Weiler, J. Am. Chem. Soc. 1974, 96, 1082, benzyl acetoacetate, 7.68 g (40 mmol) was added dropwise to a 0° C. suspension of sodium hydride (2.1 g of 50% dispersion, 42 mmol) in THF (100 mL). After stirring for 10 minutes n-butyl lithium (16 mL of 2.5 M in hexane) was added and the mixture was aged for an additional 10 minutes. At this time iodomethane (2.74 mL, 44 mmol) in THF (4 mL) was added dropwise and the mixture aged 1 hour while slowly warming to room temperature. Work-up was achieved by quenching at 0° C. with 1N HCl, extracting with ether, washing the ether with aqueous NaHCO3, brine, and drying with MgSO4. Removal of the solvent yielded benzyl 3-oxopentanoate.

Workup

  1. additionwas added
  2. waitthe mixture aged 1 hour
  3. customby quenching at 0° C. with 1N HCl
  4. extractionextracting with ether
  5. washwashing the ether with aqueous NaHCO3, brine
  6. dry with materialdrying with MgSO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-db6f33b4d57d44f385a24e130604ee9b
Source dataset
uspto-grants-1999_12
Patent number
US05998612

Reaction notes

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