Water → HCID 178469268, compound

HRID 60672Notes

Reaction equation

HRID 60672 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-22c5cc388abb47f4bc345ab380a71da8
Source dataset
uspto-grants-2016_09
Patent number
US09440974B2

Reaction notes

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