Water → 1-(1-Fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

HRID 400631Notes

Reaction equation

HRID 400631 reaction equation
[F:1][C:2]([CH:4]([OH:18])[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7])=[CH2:3].[CH2:19]([Zn]CC)C.ICI.O>C(OCC)(=O)C>[F:1][C:2]1([CH:4]([OH:18])[CH2:5][C:6]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])([CH3:8])[CH3:7])[CH2:19][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 600266102-Fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-olHCID 178418750HCID 178418750, compound

Product 1

HCID 600263391-(1-Fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol, stirred under nitrogen gas and cooled on ice, was added 8.0 mL of diethyl zinc (1.1 M in toluene). 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 2 days. Then 0.5 mL of water was added, followed by ethyl acetate, and the mixture was filtered through diatomaceous earth. The product was concentrated in vacuo and the residue was fractionated over silica gel (hexanes-dichloromethane (1:1) to dichloromethane, gradient) to give 0.8 g of 1-(1-fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol as an oil which was used without additional purification.

Workup

  1. temperaturecooled on ice
  2. customto come to room temperature
  3. stirringstirred at room temperature for 2 days
  4. filtrationthe mixture was filtered through diatomaceous earth
  5. concentrationThe product was concentrated in vacuo

Sources & evidence

ORD record
ord-a38a94b49db64afab6715a1ae93563cd
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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