Boron trifluoride etherate → HCID 86752490, compound

HRID 1600334Notes

Reaction equation

HRID 1600334 reaction equation
[B:1]([F:4])([F:3])[F:2].CCOCC.[N:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C:12](=[O:18])[CH2:11]2>C(OCC)C.CCCCCC>[N:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C:12](=[O:18])[CH2:11]2.[B:1]([F:4])([F:3])[F:2]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 195073-Quinuclidinone

Product 1

HCID 86752490HCID 86752490, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

36.5 g (257 mmol) of boron trifluoride etherate was added dropwise over 40 minutes to 33.2 g (266 mmol) of 3-quinuclidinone in 100 ml of diethyl ether and 250 ml of n-hexane. The solid which precipitated out was filtered off on a frit after 1 hour and dried to give 50.2 g (98 percent) of 3-quinuclidinone/boron trifluoride adduct in the form of a white powder. NMR data for the product: The spectra were run in d4 -methanol. The reversible addition of a solvent molecule onto the carbonylgroup resulted in the formation of a hemiacetal, whose signals are indicated below. ##EQU2##(Only the multiplicities resulting from direct 1H--13C couplings are indicated.)

Workup

  1. customThe solid which precipitated out
  2. filtrationwas filtered off on a frit after 1 hour
  3. customdried

Sources & evidence

ORD record
ord-14f7ac14f8314145a143090137f5dc2e
Source dataset
uspto-grants-1998_04
Patent number
US05744606

Reaction notes

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