Triphenylcarbinol → HCID 70456242, compound

HRID 280630Notes

Reaction equation

HRID 280630 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:14][C:15]3[NH:16][CH:17]=[CH:18][N:19]=3)[C:9]2(O)[CH3:12])=[CH:4][CH:3]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)O)C=CC=CC=1>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:14][C:15]3[NH:19][CH:18]=[CH:17][N:16]=3)=[C:9]2[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6457Triphenylcarbinol2×HCID 70457052HCID 70457052, compound

Product 1

HCID 70456242HCID 70456242, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-bromo-1-hydroxy-1-methyl-2-(1-imidazolylmethyl)-1,2,3,4-tetrahydronaphthalene (1.95 g) and triphenylmethanol (2.37 g) in trifluoroacetic acid (30 ml) was heated under reflux for 4 days. An additional 2.37 g of triphenylmethanol was added and the solution was heated under reflux for a further 5 days. The solution was evaporated and the residue was basified with diluted sodium hydroxide solution. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform first gave triphenylmethane and some triphenylmethanol followed by pure product. The product-containing fractions were evaporated to give 7-bromo-2-(1-imidazolylmethyl)-1-methylnaphthalene (1.38 g). A sample crystallised from ethyl acetate/petrol (b.p. 60°-80°) had m.p. 112°-113°.

Workup

  1. temperatureunder reflux for 4 days
  2. temperaturethe solution was heated
  3. temperatureunder reflux for a further 5 days
  4. customThe solution was evaporated
  5. extractionThe mixture was extracted several times with ethyl acetate
  6. washthe combined extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. customgave an oil which
  10. customwas chromatographed on silica gel
  11. washElution with chloroform first gave triphenylmethane
  12. customThe product-containing fractions were evaporated

Sources & evidence

ORD record
ord-3d5d8f07ede64ac483011303330111a4
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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