Water → 3-(1-Triphenylmethylimidazol-2-yl)-1-(tetrahydropyran-2-yloxy)propane

HRID 638324Notes

Reaction equation

HRID 638324 reaction equation
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.I[CH2:31][CH2:32][CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1.O>C1COCC1.CCCCCC>[C:19]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:31][CH2:32][CH2:33][O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 618231DechloroclotrimazoleHCID 110329072-(3-iodopropoxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 202534833-(1-Triphenylmethylimidazol-2-yl)-1-(tetrahydropyran-2-yloxy)propane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 310 mg (1 mmol) of 1-triphenylmethylimidazole (K H. Buchel et al.; Drugs Made in Germany, 1972, 15, 77) in 12 ml of dry THF is cooled to 0° under nitrogen and treated with 0.647 ml (1.1 mmol) of 1.7M solution of n-BuLi in hexane. The solution is stirred at room temperature for 1 hour, then recooled to 0° and treated with 405 mg (1.5 mmol) of 1-iodo-3-(tetrahydropyran-2-yloxy)propane dissolved in 2 ml of dry THF. The reaction mixture is allowed to warm to room temperature overnight, then poured into water and extracted with ethyl acetate. The organic extract is rinsed with brine and dried (MgSO4). Removal of solvents in vacuo affords the title A compound.

Workup

  1. customrecooled to 0°
  2. temperatureto warm to room temperature overnight
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washis rinsed with brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvents in vacuo
  8. customaffords the title A compound

Sources & evidence

ORD record
ord-8c99b2965d3f401d90ccab40f4d33597
Source dataset
uspto-grants-1985_12
Patent number
US04560680

Reaction notes

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