Chlorodifluoromethane → (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

HRID 1489910Notes

Reaction equation

HRID 1489910 reaction equation
C([O:5][C:6]([CH:8]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9](OCC)=O)=O)(C)(C)C.CC(C)([O-])C.[Na+].ClC(F)[F:31].O.[Cl-].[Na+].O>O1CCCC1>[F:31]/[CH:9]=[C:8](\[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)/[CH2:6][OH:5]

Participants

6

Reactant 4

HCID 6372ChlorodifluoromethaneHCID 15342050Ethyl 2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrateHCID 23676156Sodium t-butoxideHCID 23713072Sodium chloride dihydrate

Product 1

HCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Combine ethyl 2-(t-butoxycarbonyl)-4-(p-fluorophenyl)butyrate (32.14 g) and sodium t-butoxide (19.81 g) in tetrahydrofuran (400 mL). Stir the mixture for 1 hour, then heat to 45° C. Add an excess of chlorodifluoromethane over about 15 minutes. After 1 hour under an atmosphere of chlorodifluoromethane, allow the temperature to fall to ambient. Pour the reaction mixture into water/brine. Extract with diethyl ether. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. waitAfter 1 hour under an atmosphere of chlorodifluoromethane
  2. extractionExtract with diethyl ether
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-3fb3ea96d228498a8df52e44e3e177ec
Source dataset
uspto-grants-1997_10
Patent number
US05679854

Reaction notes

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