Ammonium Chloride → HCID 22285049, compound

HRID 1061873Notes

Reaction equation

HRID 1061873 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])=[C:7]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:6]=[CH:5]2.C([Li])CCC.[CH:26]([C:28]1[N:29]=[CH:30][N:31]([C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=1)=[O:27].[Cl-].[NH4+]>C1COCC1.CCCCCC>[Si:14]([O:13][C:7]1[C:8]([CH3:12])=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:26]([C:28]1[N:29]=[CH:30][N:31]([C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:32]=1)[OH:27])[CH:11]=[CH:10]2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 22018348HCID 22018348, compoundHCID 178418339Butyllithium

Product 1

HCID 22285049HCID 22285049, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

6-Bromo-2-tert-butyldimethylsilyloxy-1-methylnaphthalene (35.1 g) was dissolved in THF (350 mL) and the solution was cooled to −70° C. A solution (1.6 M: 82 mL) of n-butyllithium in hexane was slowly added dropwise and the mixture was stirred for 1 hr. Then, a solution (300 mL) of 4-formyl-1-trityl-1H-imidazole (30.5 g) in THF was added dropwise. After stirring at −70° C. for 30 min., the reaction was stopped by adding 20% aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crude (6-tert-butyldimethylsilyloxy-5-methyl-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanol as an amorphous solid.

Workup

  1. stirringAfter stirring at −70° C. for 30 min.
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-80d7c369019a4c838518dd59a0beedb5
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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