Nitrogen → 1-(2,2-Diethoxyethyl)cyclopropane

HRID 1837611

Reaction equation

HRID 1837611 reaction equation
[N+](=[CH2:3])=[N-].[CH2:4]([O:6][CH:7]([O:11][CH2:12][CH3:13])[CH2:8][CH:9]=[CH2:10])[CH3:5].N#N>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:4]([O:6][CH:7]([O:11][CH2:12][CH3:13])[CH2:8][CH:9]1[CH2:3][CH2:10]1)[CH3:5]

Participants

6

Reactant 3

HCID 947NitrogenHCID 9550DiazomethaneHCID 2564264,4-Diethoxybut-1-ene

Product 1

HCID 232645691-(2,2-Diethoxyethyl)cyclopropane

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Diazomethane (6.17 g, 147 mmol) was added dropwise to 3.02 g (21 mmol) of 3-butenal diethyl acetal in 10 ml of dry ether with intensive stirring at 0 C. Then 70 mg (0.312 mmol) of palladium (II) acetate in 50 ml of dry ether was added all at once. Then stirring at 0 C continued until the evolution of N2 ceased (10 min.). The ether was distilled off to the reduced volume of the reaction mixture ca 10 ml. The precipitate was filtered off on a fritted glass funnel and the filtrate evaporated. The crude product (2.57 g) contained 97% of the title compound (GC) and was used without further purification.

Workup

  1. stirringThen stirring at 0 C
  2. custom(10 min.)
  3. distillationThe ether was distilled off to the reduced volume of the reaction mixture ca 10 ml
  4. filtrationThe precipitate was filtered off on a fritted glass funnel
  5. customthe filtrate evaporated
  6. customwas used without further purification

Sources & evidence

ORD record
ord-ffe74f97a18947bf92a7bc54ad5bc33e
Source dataset
uspto-grants-2004_08
Patent number
US06784198B1

Linked notes

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