Boron trifluoride etherate → HCID 69591807, compound

HRID 1793652Notes

Reaction equation

HRID 1793652 reaction equation
C([Li])CCC.Br[C:7]1[C:11]([Br:12])=[C:10]([CH3:13])[S:9][C:8]=1[CH3:14].[O:15]1[CH:20]2[CH:16]1[CH2:17][O:18][CH2:19]2.B(F)(F)F.CCOCC.[Cl-].[NH4+]>C1COCC1>[Br:12][C:11]1[C:7]([C@@H:20]2[CH2:19][O:18][CH2:17][C@H:16]2[OH:15])=[C:8]([CH3:14])[S:9][C:10]=1[CH3:13]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 126263482,4-DIBROMO-3,5-DIMETHYLTHIOPHENEHCID 178418339Butyllithium

Product 1

HCID 69591807HCID 69591807, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6 M in hexane; 0.239 mol) is added dropwise to a solution of 3,4-dibromo-2,5-dimethylthiophene (0.239 mol) in 325 ml of THF which has been cooled to −78° C. and the mixture is stirred for 30 minutes. 3,4-Epoxytetrahydrofuran (0.217 mol) and boron trifluoride etherate (0.217 mol) are added dropwise to this solution. The reaction solution is warmed to 0° C. and stirred for a further 3 hours. It is subsequently hydrolyzed with saturated ammonium chloride solution and the aqueous phase is extracted twice with tert-butyl methyl ether. After drying, the solvent is removed under reduced pressure and the crude product is purified by chromatography. The product is obtained as an oil in a yield of 64%.

Workup

  1. temperatureThe reaction solution is warmed to 0° C.
  2. stirringstirred for a further 3 hours
  3. extractionthe aqueous phase is extracted twice with tert-butyl methyl ether
  4. customAfter drying
  5. customthe solvent is removed under reduced pressure
  6. customthe crude product is purified by chromatography
  7. customThe product is obtained as an oil in a yield of 64%

Sources & evidence

ORD record
ord-10712981336d48529ad7b571d5791d5b
Source dataset
uspto-grants-2006_07
Patent number
US07081533B2

Reaction notes

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