Ethylene → (R)-6-Fluoro-1-isopropyl-3,4-dihydronaphthalen-2(1H)-one

HRID 892809Notes

Reaction equation

HRID 892809 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:12]([CH3:14])[CH3:13])[C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[CH2:15]=[CH2:16].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C@@H:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[O:10])[CH2:16][CH2:15]2

Participants

5

Reactant 3

HCID 6325EthyleneHCID 6451240Aluminum(III) Chloride2×HCID 53636491[R]-(-)-2-(p-fluorophenyl)-3-methylbutyryl chloride

Product 1

HCID 53755681(R)-6-Fluoro-1-isopropyl-3,4-dihydronaphthalen-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 54.8 g (0.255 mol) of [R]-(-)-2-(p-fluorophenyl)-3-methylbutyryl chloride in 950 ml of methylene chloride was saturated at -10° with ethylene gas. The temperature was then reduced to -56° and 47.5 g (0.356 mol) of aluminum chloride in one portion were added. After 15 minutes, 10.0 g (0.075 mol) more of aluminum chloride were added thereto and the reaction mixture was left to warm slowly to -20°. Then, 500 ml of ice-water were cautiously added, and the organic phase was separated and washed with 3N hydrochloric acid and water. After drying and evaporating the solvent under reduced pressure, 59.6 g of [R]-(+)-6-fluoro-3,4-dihydro-1-isopropyl-2(1H)-naphtone were obtained as a light yellow oil; [α]D20 =+189.5° (c=1, methanol).

Workup

  1. customwas then reduced to -56°
  2. waitthe reaction mixture was left
  3. temperatureto warm slowly to -20°
  4. customthe organic phase was separated
  5. washwashed with 3N hydrochloric acid and water
  6. customAfter drying
  7. customevaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-cd838089c8634cb58875ce5cd42d6f2e
Source dataset
uspto-grants-1992_06
Patent number
US05120759

Reaction notes

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