Boron trifluoride → Butyl ether

HRID 1614429Notes

Reaction equation

HRID 1614429 reaction equation
[CH2:1]([O:5][C:6](=N)[C:7](Cl)(Cl)Cl)[CH2:2][CH2:3][CH3:4].[CH3:12][C:13](=CCC/C(=C/CO)/C)C.B(F)(F)F.C([O-])(O)=O.[Na+]>C1CCCCC1>[CH2:1]([O:5][CH2:6][CH2:7][CH2:12][CH3:13])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 637566GeraniolHCID 86746661HCID 86746661, compound

Product 1

HCID 8909Butyl ether

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

Compound (13) is prepared as follows: To a solution of 18.9 g t.butyltrichloroacetimidate in 50 ml cyclohexane is added a solution of 12.1 g geraniol (10) in 50 ml cyclohexane. After external cooling in ice is added dropwise in 15 min 0.8 ml BF3 -etherate. The reaction mixture is stirred at room temperature for 2 hours. Then 1.0 g NaHCO3 is added and the mixture is stirred for 10 min. The precipitate is filtered off and washed with hexane. After separation, washing with 5% aqueous NaHCO3 -solution and water successively, drying and evaporation to dryness, the organic phase yields 17.3 g of a product. This product is purified by flash chromatography; the desired t.butylether (13) is obtained in a yield of 11.43 g (69%). Identification by NMR: 1H-NMR(CDCl3); δ: 5.33 (t.1H); 5.09 (t.1H); 3.92 (d.2H); 2.15-1.95 (4H); 1.67 (s. 3H); 1.66(s.-3H); 1.59 (s.3H); 1.23 (s.9H).

Workup

  1. temperatureAfter external cooling in ice
  2. stirringthe mixture is stirred for 10 min
  3. filtrationThe precipitate is filtered off
  4. washwashed with hexane
  5. customAfter separation
  6. washwashing with 5% aqueous NaHCO3 -solution and water successively
  7. customdrying
  8. customevaporation to dryness

Sources & evidence

ORD record
ord-0e5f6b5be8944a67a0425ff9fcd8f8e3
Source dataset
uspto-grants-1993_03
Patent number
US05196608

Reaction notes

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