6-Oxabicyclo[3.1.0]hexane → HCID 58075730, compound

HRID 451091Notes

Reaction equation

HRID 451091 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([F:11])[C:6]([F:10])=[C:7]([F:9])[CH:8]=1.[CH:12]12[O:17][CH:16]1[CH2:15][CH2:14][CH2:13]2>C1COCC1.[Cu]I>[F:9][C:7]1[CH:8]=[C:3]([C@H:15]2[CH2:14][CH2:13][CH2:12][C@@H:16]2[OH:17])[CH:4]=[C:5]([F:11])[C:6]=1[F:10]

Participants

6

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224Magnesium

Product 1

HCID 58075730HCID 58075730, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium (2.88 g, 118 mmol) in THF (110 mL) was slowly added 5-bromo-1,2,3-trifluorobenzene (25 g, 118 mmol). After the addition, the reaction mixture was heated at reflux for 2 h. To this reaction mixture, copper (I) iodide (1.506 g, 7.91 mmol) and 6-oxabicyclo[3.1.0]hexane (9.93 g, 118 mmol) dissolved in THF (20 mL) were added dropwise. The reaction mixture warmed upon the addition of the epoxide. The reaction was stirred at rt for 2 h at rt. The reaction mixture was quenched by the addition of a solution of ammonium chloride. Ether was added and the organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to give (1S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol (20.2 g, 93 mmol, 79% yield).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2 h
  4. additionwere added dropwise
  5. customThe reaction mixture was quenched by the addition of a solution of ammonium chloride
  6. additionEther was added
  7. customthe organic layer was collected
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ba5cc9416082431b8cf5e228e09a2f24
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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