Acetone → HCID 20764334, compound

HRID 983563Notes

Reaction equation

HRID 983563 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[C:4]([OH:17])[C:3]=1[CH:18]1[CH:23]2[CH2:24][CH:21]([C:22]2([CH3:26])[CH3:25])[C:20]([C:27]([OH:29])=[O:28])=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:37][C:38](=[O:40])[CH3:39].[I-].[CH3:42][C:43]([CH3:45])=[O:44]>>[C:38]([CH2:39][O:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[C:4]([O:17][CH2:42][C:43](=[O:44])[CH3:45])[C:3]=1[CH:18]1[CH:23]2[CH2:24][CH:21]([C:22]2([CH3:26])[CH3:25])[C:20]([C:27]([OH:29])=[O:28])=[CH:19]1)(=[O:40])[CH3:37]

Participants

6

Reactant 5

HCID 180AcetoneHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 20764336HCID 20764336, compound

Product 1

HCID 20764334HCID 20764334, compoundYield 67%

Procedure

To a suspension of compound XII (0.109 g, 0.25 mmol) and potassium carbonate (0.138 g, 1 mmol) in anhydrous acetone (4 mL) was added chloroacetone (60 microliters, 0.75 mmol). The reaction mixture was stirred at reflux and a catalytic amount of potasssium iodide was added. After 3 hours, the solids were removed by filtration and washed with dichloromethane. The dichloromethane solvent was combined with the acetone filtrate and the combined solvents removed by evaporation. The resulting residue was purified on a reverse phase C-18 column using 70% acetonitrile (30% water, 0.1% acetic acid) to afford 86 mg of pure (XIII) (67% yield).

Workup

  1. temperatureat reflux
  2. customthe solids were removed by filtration
  3. washwashed with dichloromethane
  4. customthe combined solvents removed by evaporation
  5. customThe resulting residue was purified on a reverse phase C-18 column

Sources & evidence

ORD record
ord-8da2acc502394f9f8be65bd68f2fb479
Source dataset
uspto-grants-2005_03
Patent number
US06864291B1

Reaction notes

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