Imidazole → HCID 178506949, compound

HRID 514463Notes

Reaction equation

HRID 514463 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][Li:8])=[O:6].N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C=O)C>[Si:18]([O:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][Li:8])=[O:6])([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 178506948HCID 178506948, compound

Product 1

HCID 178506949HCID 178506949, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxybutanoyloxylithium (5.17 g, 41.03 mmol) and 1H-imidazole (4.19 g, 61.55 mmol) in DMF (20 mL) was added TBSCl (7.42 g, 49.04 mmol) in portions at r.t. The reaction mixture was then stirred overnight. The reaction solution was poured into water and extracted with ethyl acetate three times. The organic phase separated and washed with water twice, brine and dried with anhydrous Na2SO4. It was then concentrated to give the title compound as colorless oil (8.0 g, 89%). [M+H] Calc'd for C10H21LiO3Si, 225. Found, 225.

Workup

  1. extractionextracted with ethyl acetate three times
  2. customThe organic phase separated
  3. washwashed with water twice
  4. dry with materialbrine and dried with anhydrous Na2SO4
  5. concentrationIt was then concentrated

Sources & evidence

ORD record
ord-55fce9bbd7144888ba6b37842ba09aff
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

Loading…