Acetamide → HCID 15644271, compound

HRID 359543Notes

Reaction equation

HRID 359543 reaction equation
[CH:1]1([C:5]([OH:14])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]#[CH:7])[CH2:4][CH2:3][CH2:2]1.C(N)(=[O:17])C.[OH-].[K+]>C(O)(=O)C.C(OC(=O)C)(=O)C.C(Cl)Cl.O>[CH:1]1([C:5]([OH:14])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6](=[O:17])[CH3:7])[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 178AcetamideHCID 14797Potassium HydroxideHCID 15030052HCID 15030052, compound

Product 1

HCID 15644271HCID 15644271, compoundYield 78.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 259.9 g (1.4 mole) of 1-cyclobutyl-1-hydroxy-1-phenyl-2-propyne in 1500 mL of acetic acid and 150 mL of acetic anhydride was added 445.2 g (1.4 mole) of mercuric acetate. The mixture was stirred overnight at room temperature. The solution was diluted with 1.5 L of methylene chloride and to it was added 1.5 L of celite and 115 g of acetamide. After being stirred for 24 hours, the mixture was filtered through a pad of celite. The solid residue was washed four times with 500 mL portions of methylene chloride. The organic layers were combined, washed three times with water, three times with saturated sodium bicarbonate. The solvent was removed under reduced pressure. The residue was dissolved in 1200 mL of methanol and 102 g (1.54 mole) of potassium hydroxide was added. The mixture was brought to reflux for 2 hours and allowed to cool to room temperature. The mixture was diluted with 1500 mL of water and extracted four times with 500 mL of ether. The organic layers were combined washed three times with water, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was distilled bulb-to-bulb to give 224.5 g of 1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone, bath temperature 110° C. NMR (CDCl3) 1.7-2.2 (m, 6 H), 2.0 (s, 3 H), 3.5 (m, 1 H), 4.7 (s, 1 H), 7.2-7.5 (m, 5 H); IR (neat film) 3460, 2940, 1710, 1360, 1140, 760, 700 cm-1.

Workup

  1. stirringAfter being stirred for 24 hours
  2. filtrationthe mixture was filtered through a pad of celite
  3. washThe solid residue was washed four times with 500 mL portions of methylene chloride
  4. washwashed three times with water, three times with saturated sodium bicarbonate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in 1200 mL of methanol
  7. temperatureto reflux for 2 hours
  8. temperatureto cool to room temperature
  9. extractionextracted four times with 500 mL of ether
  10. washThe organic layers were combined washed three times with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent removed under reduced pressure
  13. distillationThe residue was distilled bulb-to-bulb

Sources & evidence

ORD record
ord-a29b5835603d468197f9ae8ca5e10986
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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