Tetrahydrofuran → HCID 11242142, compound

HRID 1443326Notes

Reaction equation

HRID 1443326 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][C:3]=1[CH2:14][CH2:15][CH3:16].O1CCCC1.C([Li])CCC.C([O:30][B:31](OC(C)C)[O:32]C(C)C)(C)C>CCCCCC>[CH2:9]([C:8]([C:5]1[CH:6]=[CH:7][C:2]([B:31]([OH:32])[OH:30])=[C:3]([CH2:14][CH2:15][CH3:16])[CH:4]=1)([OH:13])[CH2:11][CH3:12])[CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 59167145HCID 59167145, compoundHCID 178418339Butyllithium

Product 1

HCID 11242142HCID 11242142, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

In a three-necked flask, introduce under nitrogen 5 g of 3-(4-bromo-3-propylphenyl)pentan-3-ol (17.5 mmol) and 50 cm3 of tetrahydrofuran. Cool the mixture to −70° C. and add dropwise 17.5 cm3 (43.7 mmol) of a 2.5M solution of n-butyllithium in hexane, over 30 minutes. Leave the reaction mixture for approximately 2 h with stirring at −70° C. and then add dropwise 10 cm3 of triisopropylborate (43.7 mmol), over 20 minutes. Leave the reaction mixture with stirring for 4 h, allowing the temperature to increase to −40° C. Hydrolyse the mixture with saturated NH4Cl solution and extract twice with ethyl acetate. Wash the combined organic phases with saturated sodium chloride solution and evaporate the solvents under vacuum. This gives 5.4 g of a colorless oil, which is chromatographed on silica gel (heptane/ethyl acetate=3/1). This gives 1.92 g of 4-(1-ethyl-1-hydroxypropyl)-2-propylphenylboronic acid in the form of a highly viscous oil. (Yield=44%)

Workup

  1. customLeave the reaction mixture for approximately 2 h
  2. waitover 20 minutes
  3. customLeave the reaction mixture
  4. stirringwith stirring for 4 h
  5. temperatureto increase to −40° C
  6. extractionHydrolyse the mixture with saturated NH4Cl solution and extract twice with ethyl acetate
  7. washWash the combined organic phases with saturated sodium chloride solution
  8. customevaporate the solvents under vacuum
  9. customThis gives 5.4 g of a colorless oil, which is chromatographed on silica gel (heptane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-9ef030a85b8a47b1a09e09cbcd7eec59
Source dataset
uspto-grants-2010_02
Patent number
US07659421B2

Reaction notes

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