Imidazole → HCID 57771439, compound

HRID 2070592Notes

Reaction equation

HRID 2070592 reaction equation
[Br:1][CH2:2][C@@H:3]([OH:7])[CH2:4][CH2:5][Br:6].N1C=CN=C1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].O>CN(C)C=O>[Br:6][CH2:5][CH2:4][C@@H:3]([CH2:2][Br:1])[O:7][Si:17]([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 94078tert-Butyldiphenylchlorosilane2×HCID 641233HCID 641233, compound

Product 1

HCID 57771439HCID 57771439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-1,4-dibromo-2-butanol (5.0 g) in N,N-dimethylformamide (30 mL) were added imidazole (1.91 g) and tert-butylchlorodiphenylsilane (7.1 mL) under ice-cooling, followed by stirring the mixture at room temperature for 13 hours. To the reaction mixture were further added imidazole (0.59 g) and tert-butylchlorodiphenylsilane (1.77 mL), followed by stirring the mixture at room temperature for 7 hours To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:50) to give ((S)-3-bromo-1-bromomethyl-propoxy)-tert-butyldiphenylsilane (8.56 g).

Workup

  1. temperaturecooling
  2. stirringby stirring the mixture at room temperature for 7 hours To the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with 1N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:50)

Sources & evidence

ORD record
ord-cd3ccbe367ee4d1597a386e36d755293
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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