Boron trifluoride etherate → HCID 23039698, compound

HRID 2166408Notes

Reaction equation

HRID 2166408 reaction equation
B(F)(F)F.C[CH2:6][O:7]CC.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]1([CH2:21][CH3:22])[O:20][CH2:19]1>CO>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]([O:20][CH3:19])([CH2:21][CH3:22])[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 23039726HCID 23039726, compound

Product 1

HCID 23039698HCID 23039698, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.64 g of boron trifluoride-etherate, dissolved in 30 ml of methanol, are added dropwise at 4°-6° C. to a solution of 16.25 g (75 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxybutane of purity 95%, in 30 ml of methanol. The clear solution is then allowed to reach room temperature (20° C.) in a water bath and, after 16 hours, is worked up by extraction with water and chloroform. The chloroform solution is washed with NaHCO3 and dried with Na2SO4, and the solvent is removed on a rotary evaporator. This gives 19 g of crude product, which is purified by chromatography, using silica gel and a mixture of 4 parts of petroleum ether and one part of ethyl acetate. Removing the solvent at 60° C. in vacuo (20 mbar) gives 13.35 g (75.2%) of pure product in the form of a colourless oil. 60 MHz-1H-NMR (DCCl3): δ=7.1-7.6 ppm (m, 3H, aromatic); 3.7-4.6 ppm (m, --CH2OH); 3.28 ppm (s, OCH3); 1.6-2.3 ppm (m, CH2CH3, OH); 0.67 ppm (t, CH2CH3).

Workup

  1. customto reach room temperature
  2. custom(20° C.)
  3. extractionis worked up by extraction with water and chloroform
  4. washThe chloroform solution is washed with NaHCO3
  5. dry with materialdried with Na2SO4
  6. customthe solvent is removed on a rotary evaporator
  7. customThis gives 19 g of crude product, which is purified by chromatography
  8. additiona mixture of 4 parts of petroleum ether and one part of ethyl acetate
  9. customRemoving the solvent at 60° C. in vacuo (20 mbar)

Sources & evidence

ORD record
ord-6439520102454f6da55c6e02068db55b
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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