Hydrochloric Acid → HCID 58261971, compound

HRID 1618943Notes

Reaction equation

HRID 1618943 reaction equation
[C:1]1([C:7]2[CH:25]=[CH:24][C:10]3[O:11][C:12]4[CH:17]=[CH:16][C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:14][C:13]=4[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[B:31](OC)([O:34]C)[O:32]C.Cl>CCCCCC.C(OCC)(=O)C.O1CCCC1>[C:18]1([C:15]2[CH:16]=[C:17]([B:31]([OH:34])[OH:32])[C:12]3[O:11][C:10]4[CH:24]=[CH:25][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:8][C:9]=4[C:13]=3[CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 21447398HCID 21447398, compoundHCID 178418339Butyllithium

Product 1

HCID 58261971HCID 58261971, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-80 °C

Procedure

In a 200 mL three-neck flask was put 2.4 g (7.5 mmol) of 2,8-diphenyldibenzofuran. The air in the flask was replaced with nitrogen. To this mixture was added 40 mL of tetrahydrofuran (THF), and this solution was cooled to −80° C. Then, 5.6 mL (9.0 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dripped into this solution with a syringe. After that, this solution was stirred for 2 hours while its temperature was returned to room temperature. Then, this solution was again cooled to −80° C., and 1.7 mL (15 mmol) of trimethyl borate was added to this solution. This solution was stirred for 3 days while its temperature was returned to room temperature. After that, about 30 mL of diluted hydrochloric acid (1.0 mol/L) was added to this solution, followed by stirring for 1 hour. Then, the aqueous layer of this mixture was extracted with ethyl acetate, and the ethyl acetate solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated to give an oily substance, and a mixed solvent of ethyl acetate and hexane was added to the oily substance. The mixture was irradiated with ultrasonic waves, whereby a solid was precipitated. This solid was collected by suction filtration to give 2.2 g of a white powder in 82% yield, which was the substance to be produced.

Workup

  1. customIn a 200 mL three-neck flask was put
  2. customwas returned to room temperature
  3. temperatureThen, this solution was again cooled to −80° C.
  4. stirringThis solution was stirred for 3 days while its temperature
  5. customwas returned to room temperature
  6. stirringby stirring for 1 hour
  7. extractionThen, the aqueous layer of this mixture was extracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialThe organic layer was dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe resulting filtrate was concentrated
  12. customto give an oily substance
  13. customThe mixture was irradiated with ultrasonic waves, whereby a solid
  14. customwas precipitated
  15. filtrationThis solid was collected by suction filtration

Sources & evidence

ORD record
ord-52949050a24c4365b0213eb00e3d91d2
Source dataset
uspto-grants-2014_07
Patent number
US08771840B2

Reaction notes

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