Potassium Hydroxide → 6-(4-Aminophenyl)hex-5-yn-1-ol

HRID 1944877Notes

Reaction equation

HRID 1944877 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:7]=1)=O.[OH-].[K+]>CC(O)C>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 575169382,2,2-trifluoro-N-(4-(6-hydroxyhex-1-yn-1-yl)phenyl)acetamide

Product 1

HCID 112292476-(4-Aminophenyl)hex-5-yn-1-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of Intermediate 39 (8.5 mmol) in IPA (20 mL) was added to a 100° C. solution of potassium hydroxide (1.4 g, 26 mmol) in IPA (150 mL). The mixture was henceforth heated to reflux for 3.5 hours before being concentrated to drying under reduced pressure. The residue was partitioned between water and dichloromethane. The aqueous phase was extracted three times with dichloromethane. The combined extracts were concentrated to dryness under reduced pressure, and the resulting residue was purified via automated flash silica gel chromatography, using a 25 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound as a pale blond oil. ES/MS calcd. for C12H16NO+: 190.1. Found m/z=190.2 (M+H)+

Workup

  1. temperatureThe mixture was henceforth heated
  2. temperatureto reflux for 3.5 hours
  3. concentrationbefore being concentrated
  4. customto drying under reduced pressure
  5. customThe residue was partitioned between water and dichloromethane
  6. extractionThe aqueous phase was extracted three times with dichloromethane
  7. concentrationThe combined extracts were concentrated to dryness under reduced pressure
  8. customthe resulting residue was purified via automated flash silica gel chromatography

Sources & evidence

ORD record
ord-88bea529e1da43ad9940a5f38adef675
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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