Water → 1-{3-[2-(1-Benzothiophen-5-yl)ethoxy]propyl}-3-(trityloxy)azetidine

HRID 7457Notes

Reaction equation

HRID 7457 reaction equation
[OH-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][OH:14])=[CH:11][C:6]=2[CH:5]=[CH:4]1.C(O)(=O)C(O)=O.Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:28][CH:27]([O:29][C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26]1.O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][O:14][CH2:22][CH2:23][CH2:24][N:25]3[CH2:26][CH:27]([O:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:28]3)=[CH:11][C:6]=2[CH:5]=[CH:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-olHCID 219900961-(3-Chloropropyl)-3-(trityloxy)azetidine oxalate

Product 1

HCID 219900541-{3-[2-(1-Benzothiophen-5-yl)ethoxy]propyl}-3-(trityloxy)azetidineYield 36.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

In a mixture of 0.4 mL of toluene and 7 mL of a 50% (W/V) aqueous sodium hydroxide solution was suspended 0.54 g of 2-(1-benzothiophen-5-yl)-1-ethanol, followed by adding thereto 1.45 g of 1-(3-chloropropyl)-3-(trityloxy)azetidine oxalate and 0.03 g of tetra-n-butylammonium bromide, and the resulting mixture was refluxed for 7 hours. After the reaction mixture was cooled, water and toluene were added thereto and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=75:1) to obtain 0.59 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-(trityloxy)azetidine as a light-yellow oil.

Workup

  1. additionby adding
  2. temperatureAfter the reaction mixture was cooled
  3. customthe organic layer was separated
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=75:1)

Sources & evidence

ORD record
ord-418ee189789f42de93dac3320c3963b2
Source dataset
uspto-grants-2006_08
Patent number
US07087594B2

Reaction notes

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