3,3-Diethoxypropyne → HCID 67168825, compound

HRID 877376Notes

Reaction equation

HRID 877376 reaction equation
[N:1]([CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])=[N+:2]=[N-:3].[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[C:13]#[CH:14])[CH3:10].[Na].C(O)CCC.O>O>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[C:13]1[N:3]=[N:2][N:1]([CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])[CH:14]=1)[CH3:10]

Participants

6

Reactant 4

HCID 662853,3-DiethoxypropyneHCID 150751Trimethylsilylmethyl AzideHCID 5360545SodiumHCID 22253497Water butanol

Product 1

HCID 67168825HCID 67168825, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml round bottom flask equipped with a magnetic stir bar were added (azidomethyl)(trimethyl)silane (1.000 g, 7.740 mmol), 3,3-diethoxyprop-1-yne (0.992 g, 7.740 mmol), freshly made 1.0N sodium asorbate (0.774 ml, 7.740 mmol), and 1.0N Cu2SO4 (0.774 ml, 7.740 mmol) into 30.0 ml of a mixed solvent BuOH/H2O (1:1). The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum to give the crude title compound as a light yellow liquid (1.620 g, 81% crude). ES-MS [M+1]+: 258.1 (M+H). This intermediate was carried over to the next step without further purifications and characterizations.

Workup

  1. customTo a 100 ml round bottom flask equipped with a magnetic stir bar
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-b30fe5180f9f48e19ae90353e89c3ce4
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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