Ethanol → HCID 25073916, compound

HRID 237868Notes

Reaction equation

HRID 237868 reaction equation
[CH:1]1([C:7]2[CH:21]=[CH:20][C:10]([O:11][CH2:12][C:13]3([CH3:19])[O:17][C:16](=[NH:18])[NH:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](OCC)(=[O:25])[C:23]#[CH:24].C(O)C>C(O)(C)(C)C>[CH:1]1([C:7]2[CH:21]=[CH:20][C:10]([O:11][CH2:12][C:13]3([CH3:19])[O:17][C:16]4=[N:18][C:22](=[O:25])[CH:23]=[CH:24][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 12182Ethyl propiolateHCID 178431161HCID 178431161, compound

Product 1

HCID 25073916HCID 25073916, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 5-(4-cyclohexyl-phenoxymethyl)-5-methyl-oxazolidin-2-ylideneamine (1.11 g, 3.85 mmol) in 15 ml of t-butanol was heated to 80° C. All of the suspension dissolved. Ethyl propiolate (0.51 ml, 5.0 mmol) was added followed by 5 ml of ethanol. The reaction mixture was heated at reflux for 8 hrs. An off-white precipitate gradually came out of the solution. The reaction was cooled to room temperature and the solid isolated by filtration and washed with ether to provide the title compound as a white solid. Yield 0.75 g.

Workup

  1. dissolutionAll of the suspension dissolved
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 8 hrs
  4. temperatureThe reaction was cooled to room temperature
  5. customthe solid isolated by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-b4141969055c48b88587291019491a39
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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