Diazomethane → HCID 22235737, compound

HRID 1744148Notes

Reaction equation

HRID 1744148 reaction equation
[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+](=[CH2:13])=[N-]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][C:2]1([CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:13][CH2:1]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 3416433Ethyl 4-methyl-4-pentenoate

Product 1

HCID 22235737HCID 22235737, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To an ice cold solution of ethyl 4-methyl-4-pentenoate (1.11 g, 7.8 mmol) in 0.5 M diazomethane in Et2O, was added palladium(II) acetate by portionwise addition (4 portions of 5 mg each were added in 15 min intervals). A total of 4 portions were added. The reaction mixture was filtered on a pad of celite and concentrated under 60 mm Hg with gentle warming. This crude product was treated a second time with diazomethane and palladium(II) acetate, filtered and concentrated. The resulting oil was filtered on a pad of florisil (60–100 mesh), washed with Et2O (2×10 mL), concentrated under 60 mm Hg to give ethyl 3-(1-methylcyclopropyl)propanoate as a colorless oil.

Workup

  1. additionby portionwise addition (4 portions of 5 mg each were added in 15 min intervals)
  2. additionA total of 4 portions were added
  3. filtrationThe reaction mixture was filtered on a pad of celite
  4. concentrationconcentrated under 60 mm Hg with gentle warming
  5. additionThis crude product was treated a second time with diazomethane and palladium(II) acetate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe resulting oil was filtered on a pad of florisil (60–100 mesh)
  9. washwashed with Et2O (2×10 mL)
  10. concentrationconcentrated under 60 mm Hg

Sources & evidence

ORD record
ord-3eed97af006a419ebac1c3da9a8d28d9
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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