Ethyl Acetate → HCID 58081193, compound

HRID 928378Notes

Reaction equation

HRID 928378 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[C:17]([O:21][CH3:22])(=[O:20])[C:18]#[CH:19].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(OCC)(=O)C>CC(O)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:22][O:21][C:17]([C:18]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][CH:6]=2)[CH:19]=1)=[O:20]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 13536Methyl propiolateHCID 11031077HCID 11031077, compoundHCID 23667548Sodium Ascorbate

Product 1

HCID 58081193HCID 58081193, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-Azidomethyl-biphenyl (145 mg, 0.5 mmol), methyl propiolate (44 mg, 0.5 mmol), copper(II) sulfate (17 mg, 0.1 mmol) and sodium ascorbate (103 mg, 0.5 mmol) in 3 mL tBuOH and 1 mL water was stirred at room temperature for 3 h. Ethyl acetate was added and the mixture was extracted with water. The organic layer was dried over MgSO4 and evaporated in vacuo to give the title compound which was used in the next step without further purification. LCMS (method A) RtA=1.964 min; [M+H]+=294.0.

Workup

  1. extractionthe mixture was extracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-eec500f613c440959074fb250f917a74
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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