Boron trifluoride → 3-Carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione

HRID 975494Notes

Reaction equation

HRID 975494 reaction equation
[C:1]12([CH3:12])[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[C:4](=[O:5])[C:2]2=[O:3].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-].B(F)(F)F>CCOCC>[C:16]([CH:15]1[C:4](=[O:5])[CH:6]2[C:9]([CH3:10])([CH3:11])[C:1]([CH3:12])([CH2:8][CH2:7]2)[C:2]1=[O:3])([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12192Ethyl diazoacetateHCID 25208Bornane-2,3-dione

Product 1

HCID 189798163-Carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (±) camphorquinone [(1,7,7)-trimethylbicyclo[3,2,1]-heptane-2,3-dione](15.0 g, 90.24 mmol) and ethyl diazoacetate (11.8 g, 103.7 mmol) in 120 ml of ether is added, at 0°, BF3.ether (4 ml). The mixture is stirred at RT for 24 hr. The reaction mixture is extracted with 5% K2CO3 /H2O until no polar ethyl carboxyl dione remains. The combined aqueous extracts are acidified with conc. HCl and extracted with ether. The combined organic extracts are dried and evaporated to dryness to give crystalline 3-carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione.

Workup

  1. extractionThe reaction mixture is extracted with 5% K2CO3 /H2O until no polar ethyl carboxyl dione
  2. extractionextracted with ether
  3. customThe combined organic extracts are dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-48977ea58c864b48b4d0bb018c160553
Source dataset
uspto-grants-1997_03
Patent number
US05608101

Reaction notes

Loading…