Diethyl Ether → Ethyl 5,5-dimethylhex-2-enoate

HRID 1737152Notes

Reaction equation

HRID 1737152 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4]O.[Cr](Cl)([O-])(=O)=[O:9].[NH+]1C=CC=CC=1.[CH3:19][CH2:20][O:21][CH2:22][CH3:23]>ClCCl>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=[CH:19][C:20]([O:21][CH2:22][CH3:23])=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 122333,3-Dimethyl-1-butanolHCID 178418287HCID 178418287, compound

Product 1

HCID 54091983Ethyl 5,5-dimethylhex-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-dimethyl butan-1-ol (1.3 g) was stirred for 2 hours in dichloromethane (30 ml) with pyridinium chlorochromate (5.5 g) at room temperature, diluted with ether and filtered. Wittig reagent Ph3P=CH--CO2C2H5 (carbethoxymethylenetriphenylphosphorane)(3.6 g) was added to the filtrate and stirred overnight. The mixture was evaporated under vacuum and the residue purified by silica gel chromatography to yield 1.25 g of ethyl 5,5-dimethylhex-2-enoate.

Workup

  1. filtrationfiltered
  2. additionwas added to the filtrate
  3. customThe mixture was evaporated under vacuum
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-296441955bf6469982225a03dc90fd0a
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

Loading…