Acetone → HCID 22123610, compound

HRID 1859345Notes

Reaction equation

HRID 1859345 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].O[C:6]1C=CC=[CH:8][C:7]=1[CH:12]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][O:24][CH3:25])=[CH:19][CH:20]=2)[S:15][CH2:14][C:13]1([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=1)[CH3:26].Br[CH2:38][CH2:39][CH2:40][CH2:41][Cl:42].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:42][CH2:41][CH2:40][CH2:39][CH2:38][O:3][C:2]1[CH:4]=[CH:8][C:7]([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][O:24][CH3:25])=[CH:19][CH:20]=3)[S:15][CH2:14][C:13]2([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:31][CH:32]=2)[CH3:26])=[CH:6][CH:1]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 22123587HCID 22123587, compound

Product 1

HCID 22123610HCID 22123610, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetone solution (2 ml) of (3RS,4RS)-4-(hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman (70 mg, 0.15 mmol) were added 1-bromo-4-chlorobutane (36 μl, 0.31 mmol) and potassium carbonate (64 mg, 0.46 mmol), and the resulting mixture was heated under refluxing for 20 hours. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified using silica gel plate (ethyl acetate:hexane=1:2) to obtain 73 mg (yield: 87%) of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder refluxing for 20 hours
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe crude product thus obtained
  9. customwas purified

Sources & evidence

ORD record
ord-d2ba13071739490a9c844ad35a1a433e
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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