Imidazole → HCID 11383144, compound

HRID 1855310Notes

Reaction equation

HRID 1855310 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([O:14][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57438970HCID 57438970, compound

Product 1

HCID 11383144HCID 11383144, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing (S)-1-(4-Bromo-phenyl)-hexan-1-ol in CH2Cl2 at ambient temperature (˜23° C.) was added imidazole and t-butyldimethylsilyl chloride. The reaction mixture was stirred at ambient temperature for a period of time until all starting material was consumed before quenching with a mixture of MeOH and water. The organic layer was washed with deionized water and concentrated under reduced pressure to give the product as a yellow oil.

Workup

  1. customwas consumed
  2. custombefore quenching with a mixture of MeOH and water
  3. washThe organic layer was washed with deionized water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6665e1100c9e44fbb567d7b13981ac31
Source dataset
uspto-grants-2015_02
Patent number
US08962863B2

Reaction notes

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