Hydrochloric Acid → HCID 25132451, compound

HRID 339619Notes

Reaction equation

HRID 339619 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[B:6]([O:15][CH:16]([CH3:18])C)([O:11]C(C)C)OC(C)C.Cl.[C:20]([O:23][CH2:24][CH3:25])(=O)[CH3:21].[O:26]1CCC[CH2:27]1>O>[OH:26][CH2:27][CH2:25][CH2:24][O:23][C:20]1[C:21]2[B:6]([OH:11])[O:15][CH2:16][C:18]=2[CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21531Triisopropyl borateHCID 178418339Butyllithium

Product 1

HCID 25132451HCID 25132451, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the compound obtained above (9.98 g, 23.3 mmol) in tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 18 mL) and triisopropyl borate (8.0 mL, 35 mmol) at −78° C. under nitrogen atmosphere, and the mixture was allowed to warm to room temperature and stirred for overnight. Then hydrochloric acid (6 mol/L, 10 mL) was added, and the mixture was stirred for 30 min at room temperature. The mixture was poured into ethyl acetate and water. The organic layer was washed with brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (7:3 to 6:4 hexane/ethyl acetate) to give 7-(3-Hydroxypropoxy)benzo[c][1,2]oxaborol-1(3H)-ol (2.06 g, 43%).

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (7:3 to 6:4 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-22d725b3c59d40778ba74fb723af7a85
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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