Sodium Hydroxide → (2-(1,1-Dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662331Notes

Reaction equation

HRID 1662331 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705757Methyl 2-(1,1-dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706653(2-(1,1-Dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of 12.1 (1.01 g, 3.38 mmol) in dry THF (10.0 mL) at 0° C., was added LAH (1.0 M solution in THF (6.7 mL, 6.7 mmol)). Upon complete addition, the reaction was allowed to warm to room temperature and monitored by TLC and LCMS. Upon completion, 1N NaOH (5 mL) was carefully added to quench the reaction. The resulting solution was extracted with EtOAc (3×10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-40% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 12.2 as a colorless oil (0.82, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 7.56 (1H, s), 7.29 (1H, t, J=3.8 Hz), 7.24 (1H, m), 7.07 (1H, d, J=7.6 Hz), 6.93 (2H, m), 6.86 (1H, d, J=1.5 Hz), 4.77 (2H, s), 3.85 (3H, s), 1.72 (1H, s), 1.26 (9H, s).

Workup

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction
  4. extractionThe resulting solution was extracted with EtOAc (3×10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-40% EtOAc in hexanes)
  9. additionFractions containing the desired product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-936b59f5844b49b68ea89bb81b2186ef
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…