Water → HCID 70873408, compound

HRID 2172238Notes

Reaction equation

HRID 2172238 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([O:16][CH2:17][CH2:18][C:19]1([CH3:22])[CH2:21][O:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F:23][C:24]([F:48])([F:47])[O:25][C:26]1[CH:46]=[CH:45][C:29]([CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][N:35]([C:38]3[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=3)[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.O>C(O)C>[CH2:9]([O:16][CH2:17][CH2:18][C:19]([CH3:22])([OH:20])[CH2:21][O:44][C:41]1[CH:40]=[CH:39][C:38]([N:35]2[CH2:34][CH2:33][CH:32]([CH2:31][CH2:30][C:29]3[CH:28]=[CH:27][C:26]([O:25][C:24]([F:47])([F:23])[F:48])=[CH:46][CH:45]=3)[CH2:37][CH2:36]2)=[CH:43][CH:42]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 13683259HCID 13683259, compoundHCID 67275754HCID 67275754, compound

Product 1

HCID 70873408HCID 70873408, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A tripotassium phosphate (0.44 g, 2.1 mmol) was added to a solution of 2-[2-(Benzyloxy)ethyl]-2-methyloxirane (1.00 g, 5.2 mmol) and 4-{4-[4-(trifluoromethoxy)phenethyl]piperidin-1-yl}phenol (2.28 g, 6.2 mmol) in ethanol (10 ml), and then the mixture was heated at reflux overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→50:50) to afford the title compound as a brown powder (2.43 g, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→50:50)

Sources & evidence

ORD record
ord-8c338f6e516347e18cbf405e765ab7b6
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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