Lithium borohydride → 2-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropan-1-ol

HRID 1025807Notes

Reaction equation

HRID 1025807 reaction equation
[BH4-].[Li+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:15]2[CH:33]=[CH:32][C:18]([O:19][C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)([CH3:25])[C:21](OC)=[O:22])=[CH:17][CH:16]=2)([CH3:14])[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1>C1COCC1>[I:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:15]2[CH:16]=[CH:17][C:18]([O:19][C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)([CH3:25])[CH2:21][OH:22])=[CH:32][CH:33]=2)([CH3:14])[CH:11]([CH3:13])[CH3:12])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58381237Methyl 2-{4-[1-(4-iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropanoate

Product 1

HCID 583812432-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (1 equiv) is added to a stirred solution of 5d (1 equiv) in THF at room temperature. After completion of reaction, the reaction mixture is quenched with 2 N HCl, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5e.

Workup

  1. customAfter completion of reaction
  2. customthe reaction mixture is quenched with 2 N HCl
  3. additionpoured into saturated aqueous sodium bicarbonate
  4. extractionextracted three times with EtOAc
  5. washThe combined organic extracts are washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-23e353830e2743149b9efea4e857d1a1
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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