Aluminium lithium hydride → (2'-Fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662341Notes

Reaction equation

HRID 1662341 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](OC)=[O:17])=[CH:12][C:11]=1[O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57707262Methyl 2'-fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706867(2'-Fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-yl)methanolYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 26.3 (1.61 g, 4.47 mmol) in THF (10 mL) at 0° C., was added LAH (1.0M solution in THF, 6.70 mL, 6.70 mmol). The reaction was stirred for one hour and then carefully diluted with water, extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered, and concentrated to provide 26.4 (0.990 g, 66.7% yield).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-196c61ab75094747999b4bbcd2b88480
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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