Boron trifluoride etherate → HCID 12094930, compound

HRID 1373991Notes

Reaction equation

HRID 1373991 reaction equation
[C:1]12([C:7]3[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=3)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:6][CH:5]1[CH2:4][CH2:3][CH2:2]2.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][CH:1]1[C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 12094929HCID 12094929, compound

Product 1

HCID 12094930HCID 12094930, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4 g (17.2 mmol) of ethyl 3-(6-oxabicyclo[3.1.0]hex-1-yl)benzoate (6) and 50 ml of methylene chloride are introduced into a round-bottomed flask. The mixture is cooled to 0° C. and then 2.2 ml (17.2 mmol) of BF3.Et2O are added dropwise. The reaction mixture is stirred at 0° C. for 1 hour and then 25 ml of a saturated aqueous sodium bicarbonate solution are added. The mixture is separated by settling and the aqueous phase extracted with methylene chloride. The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). The title product is obtained in the form of a pale yellow oil (3.4 g).

Workup

  1. customThe mixture is separated
  2. extractionthe aqueous phase extracted with methylene chloride
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 80/20)

Sources & evidence

ORD record
ord-84c100dfcf5a4d2d82dd55b36fc5f457
Source dataset
uspto-grants-2007_01
Patent number
US07163957B2

Reaction notes

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