Ethyl Acetate → 1-Benzhydryl-3-(benzo[b]thiophen-3-yloxy)azetidine

HRID 634024Notes

Reaction equation

HRID 634024 reaction equation
[S:1]1[CH:5]=[C:4]([OH:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.C(=O)([O-])[O-].[K+].[K+].[CH:17]([N:30]1[CH2:33][CH:32](I)[CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)(=O)C>COCCOC.O>[CH:17]([N:30]1[CH2:33][CH:32]([O:6][C:4]2[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[S:1][CH:5]=2)[CH2:31]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10629Benzo(b)thiophene-3-olHCID 11430Potassium CarbonateHCID 73306101-Benzhydryl-3-iodoazetidine

Product 1

HCID 683381061-Benzhydryl-3-(benzo[b]thiophen-3-yloxy)azetidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

Benzo[b]thiophen-3-ol (215 mg, 1.43 mmol) and potassium carbonate (237 mg, 1.72 mmol) were successively added to a solution of 1-benzhydryl-3-iodoazetidine (500 mg, 1.43 mmol) in a mixture of 1,2-dimethoxyethane (12 mL) and water (6 mL) at room temperature. The reaction mixture was then heated up to 95° C. and stirred for 3 hours. After cooling down to room temperature, the reaction mixture was diluted by addition of water (50 mL) and ethyl acetate (50 mL). The aqueous phase was separated and extracted with ethyl acetate (5×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (2×50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (1:0 to 9:1) as eluent. The title compound was obtained as a yellow oil (220 mg, 21%).

Workup

  1. temperatureAfter cooling down to room temperature
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate (5×50 mL)
  4. washThe combined organic phases were washed with a saturated solution of sodium chloride (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c106975e2a7d48aa8c427f47f6284fb1
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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