Lithium borohydride → HCID 66789951, compound

HRID 1510133Notes

Reaction equation

HRID 1510133 reaction equation
[CH:1]1([CH:4]([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10](OC)=[O:11])[CH3:5])[CH2:3][CH2:2]1.[BH4-].[Li+]>O1CCCC1>[CH:1]1([CH:4]([O:6][C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][CH:16]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66789913HCID 66789913, compound

Product 1

HCID 66789951HCID 66789951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-(1-cyclopropylethoxy)benzoate (11.7 g, 53.1 mmol) in tetrahydrofuran (212 mL) was added lithium borohydride (80.0 ml, 159 mmol). The reaction was heated at 50° C. for twelve hours. The reaction was quenched with methanol. The solvents were concentrated. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3. The aqueous layer was extracted three times with dichloromethane and the organics were combined, washed twice with water, dried with MgSO4, filtered, and concentrated. The enantiomers were resolved on the chiral OD column (10 cm) with a flow rate of 300 ml/mn wavelength 275 nm running 97/3 hexanes/ethanol as the solvent system.

Workup

  1. customThe reaction was quenched with methanol
  2. concentrationThe solvents were concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3
  5. extractionThe aqueous layer was extracted three times with dichloromethane
  6. washwashed twice with water
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0fa8603c74284afd9246837947dc3ae7
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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