Acetic acid, azido-, ethyl ester → HCID 89027390, compound

HRID 1753085Notes

Reaction equation

HRID 1753085 reaction equation
[CH:1]1([C:4]#[CH:5])[CH2:3][CH2:2]1.[N:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N+:7]=[N-:8]>C(#N)C.[Cu](I)I.C(N(CC)CC)C>[CH:1]1([C:4]2[N:8]=[N:7][N:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 69480Acetic acid, azido-, ethyl esterHCID 138823Cyclopropylacetylene

Product 1

HCID 89027390HCID 89027390, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

Cyclopropylacetylene (15 g, 0.116 mol), ethyl azidoacetate (11.5 g, 0.174 mol), triethylamine (0.32 mL, 2.33 mmol) and copper iodide (442 mg, 2.33 mmol) in acetonitrile (100 mL) were stirred at 25° C. for 18 hours. The mixture was evaporated in vacuo and the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic phase was dried over sodium sulfate, evaporated in vacuo and purified by silica gel column chromatography eluting with EtOAc: Hexane 40: 60 to afford the title compound as a colorless liquid (95%, 21.6 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated in vacuo
  5. custompurified by silica gel column chromatography
  6. washeluting with EtOAc: Hexane 40: 60

Sources & evidence

ORD record
ord-619a2c7b77cf4046a98c8e0c07448b56
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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