Water → HCID 25166340, compound

HRID 2098502Notes

Reaction equation

HRID 2098502 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH:8]([OH:20])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH2:17][CH2:18][OH:19])[CH:10]=1)=O.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH2:5][CH2:6][CH2:7][CH:8]([C:9]1[CH:10]=[C:11]([C:15]#[C:16][CH2:17][CH2:18][OH:19])[CH:12]=[CH:13][CH:14]=1)[OH:20]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86635857HCID 86635857, compound

Product 1

HCID 25166340HCID 25166340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of, 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(4-hydroxybut-1-ynyl)phenyl)propyl)acetamide, potassium carbonate (1.6 g, 11.5 mmol) and water (3 mL) in MeOH (15 mL) was heated under reflux for 4 h. Reaction mass was concentrated to dryness under reduced pressure to give 4-(3-(3-amino-1-hydroxypropyl)phenyl)but-3-yn-1-ol as pale yellow oil after purification by flash chromatography with 15% MeOH—NH3 (9.5:0.5)-DCM. Yield (0.38 g, 60%). This compound was utilized as such for the next transformation.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customReaction mass
  4. concentrationwas concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-48f66e078760470db2105c0a0cff7f5a
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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