Water → HCID 178469268, compound

HRID 711193Notes

Reaction equation

HRID 711193 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].C[Si]([CH:12]=[N+:13]=[N-:14])(C)C.O>C1COCC1>[CH2:6]([O:5][C:1]([C:2]1[CH:3]=[CH:12][NH:13][N:14]=1)=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 12182Ethyl propiolateHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 178469268HCID 178469268, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl propiolate (10.0 g, 0.10 mol) in THF (67 mL) was treated dropwise with (trimethylsilyl)diazomethane (51 mL, 0.10 mol) maintaining the temperature between 20-30° C. with ice bath cooling. The mixture was stirred at RT for 4 h then treated cautiously with water (250 mL) with cooling in an ice bath. The organics were evaporated in vacuo and the resulting precipitate was collected by filtration, washed with water and dried at RT in vacuo to give the title compound (13.5 g, 94%). LCMS (Method 3): Rt 2.22 min, m/z 141 [MH+].

Workup

  1. temperaturecooling
  2. temperaturewith cooling in an ice bath
  3. customThe organics were evaporated in vacuo
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried at RT in vacuo

Sources & evidence

ORD record
ord-722841b5e34642639b4346f0ca5c11bd
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

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