3',4',5'-Trifluoroacetophenone → HCID 57830662, compound

HRID 1436117Notes

Reaction equation

HRID 1436117 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[CH3:23][C:24]([C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=1)=[O:25]>C1COCC1>[F:32][C:30]1[CH:31]=[C:26]([C@H:24]([OH:25])[CH3:23])[CH:27]=[C:28]([F:34])[C:29]=1[F:33]

Participants

4

Reactant 2

HCID 27769073',4',5'-TrifluoroacetophenoneHCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)borane

Product 1

HCID 57830662HCID 57830662, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (+)-DIP-chloride (11.8 g) in THF (200 ml) cooled to −30° C., 3,4,5-trifluoroacetophenone (5.0 g) [CAS 220141-73-1] was added dropwise in a nitrogen atmosphere. The reaction solution was stirred at the same temperature for five hours and at room temperature at one hour, and then THF was evaporated under reduced pressure. 6.5 ml of diethanolamine was added dropwise to a solution of the resulting residue in diethyl ether (150 ml), and the reaction solution was stirred at room temperature overnight. The insoluble matter was removed by filtration, and then the solvent was evaporated. Hexane was added to the resulting residue, and the insoluble matter was removed by filtration again. The filtrate was purified by silica gel column chromatography (heptane:ethyl acetate=19:1 to 4:1) to obtain 3.69 g of the title compound.

Workup

  1. customTHF was evaporated under reduced pressure
  2. addition6.5 ml of diethanolamine was added dropwise to a solution of the resulting residue in diethyl ether (150 ml)
  3. stirringthe reaction solution was stirred at room temperature overnight
  4. customThe insoluble matter was removed by filtration
  5. customthe solvent was evaporated
  6. additionHexane was added to the resulting residue
  7. customthe insoluble matter was removed by filtration again
  8. customThe filtrate was purified by silica gel column chromatography (heptane:ethyl acetate=19:1 to 4:1)

Sources & evidence

ORD record
ord-65d8b3469c5543729eaba1811b9c0dea
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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