Water → HCID 60026890, compound

HRID 400626Notes

Reaction equation

HRID 400626 reaction equation
[F:1][C:2]([CH:4]([OH:16])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([CH3:8])[CH3:7])=[CH2:3].[CH2:17]([Zn]CC)C.ICI.O>C(OCC)(=O)C>[F:1][C:2]1([CH:4]([OH:16])[CH2:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)([CH3:8])[CH3:7])[CH2:17][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 600266962-Fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-olHCID 178418750HCID 178418750, compound

Product 1

HCID 60026890HCID 60026890, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the above crude 2-fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol (1.73 g, 7.65 mmol) stirred under nitrogen gas and cooled on ice, was added diethyl zinc (1.1 M in toluene, 8.0 mL). After 5 minutes, 1.0 mL of diiodomethane was added dropwise over 20 minutes and the mixture was stirred and allowed to come to room temperature and then stirred at room temperature for 4 days. 0.5 mL of water was then added to the reaction mixture, followed by ethyl acetate. The resulting mixture was then filtered through diatomaceous earth and the solvent was removed in vacuo and the residue was fractionated over silica gel (hexanes-dichloromethane (1:1) to dichloromethane gradient) to give 1-(1-fluorocyclopropyl)-3-(4-fluorophenyl)-3-methylbutan-1-ol as an oil.

Workup

  1. temperaturecooled on ice
  2. customto come to room temperature
  3. stirringstirred at room temperature for 4 days
  4. filtrationThe resulting mixture was then filtered through diatomaceous earth
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1535e171f5ec4c55aa832806c599c3d4
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

Loading…