Water → HCID 58452602, compound

HRID 70566

Reaction equation

HRID 70566 reaction equation
[OH-].[K+].Br[CH2:4][CH:5]([CH3:7])[CH3:6].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1.O>CS(C)=O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][CH2:4][CH:5]([CH3:7])[CH3:6])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 14797Potassium HydroxideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 58452602HCID 58452602, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium hydroxide (1.32 g) and 1-bromo-2-methylpropane (1.04 mL) were added to a solution of 2-(4-bromophenyl)ethylalcohol (140 μL) in dimethyl sulfoxide (2 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (180 mg, 70%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. filtrationThe organic layer was filtered through diatomaceous earth
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane only)

Sources & evidence

ORD record
ord-e7e49ce9aa2a40a69c28271e7938841f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

Loading…