Water → 1-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

HRID 1061869Notes

Reaction equation

HRID 1061869 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C([Li])CCC.[CH:25]([C:28]([C:30]1[N:31]=[CH:32][N:33]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=1)=[O:29])([CH3:27])[CH3:26].O>C1COCC1.CCCCCC>[Si:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:28]([C:30]1[N:31]=[CH:32][N:33]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:34]=1)([OH:29])[CH:25]([CH3:27])[CH3:26])[CH:11]=[CH:10]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 220184421-(6-tert-butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanolYield 90.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

6-Bromo-2-tert-butyldimethylsilyloxynaphthalene (60.0 g) was dissolved in THF (600 mL) and the solution was cooled to −70° C. A solution (1.6 M: 111 mL) of n-butyllithium in hexane was slowly added dropwise and the mixture was stirred for 30 min. Then a solution (200 mL) of isopropyl(1-trityl-1H-imidazol-4-yl)ketone (52.1 g) in THF was added dropwise. The mixture was stirred at −70° C. for 30 min. and water was added to stop the reaction. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to give the title compound (79.5 g) as a colorless powder.

Workup

  1. stirringThe mixture was stirred at −70° C. for 30 min.
  2. customthe reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water and saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-40cd567c20ca4a71b9f46177f3f5f678
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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