Tetrahydrofuran → HCID 22624292, compound

HRID 279062

Reaction equation

HRID 279062 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[CH:9][C:10]=1Br)([CH3:3])[CH3:2].O1CCCC1.C([Li])CCC.[B:23](OCC)([O:27]CC)[O:24]CC>CCCCCC>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[CH:9][C:10]=1[B:23]([OH:27])[OH:24])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9009Triethyl borateHCID 22624303HCID 22624303, compoundHCID 178418339Butyllithium

Product 1

HCID 22624292HCID 22624292, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a 125 mL 3N round-bottomed flask equipped with N2 inlet and septum were added 3.59 g (15.7 mmol) 3-isopropoxy-4-bromotoluene and 30 mL dry tetrahydrofuran. The solution was cooled to −70° C. and 7.5 mL (18.8 mmol) of a 2.5 M solution of butyl lithium in hexane was added over 5 minutes, and the solution stirred 5 minutes at −70° C. Then 3.2 mL (18.8 mmol) triethyl borate was added, followed by stirring for 5 minutes at −70° C. and then stirring at room temperature for 24 hours. The reaction was quenched with 1 N aqueous hydrochloric acid and extracted into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated. The residue was triturated with hexane to a white solid, 1.7 g (56%).

Workup

  1. customTo a 125 mL 3N round-bottomed flask equipped with N2 inlet
  2. stirringby stirring for 5 minutes at −70° C.
  3. stirringstirring at room temperature for 24 hours
  4. customThe reaction was quenched with 1 N aqueous hydrochloric acid
  5. extractionextracted into ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was triturated with hexane to a white solid, 1.7 g (56%)

Sources & evidence

ORD record
ord-2a0aa955bf4f45e48947f45cd21b619f
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Linked notes

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