Aluminium lithium hydride → (2-(Butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662320Notes

Reaction equation

HRID 1662320 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([C:12](OCCCC)=[O:13])[CH:9]=[CH:8][C:7]=1[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[F:27])[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[F:27])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57705770Butyl 2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57707020(2-(Butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5.2 (1.1530 g, 3.079 mmol) in THF (10 mL) at 0° C. was added LAH (1.0 M solution in THF (4.619 mL, 4.619 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 5.3 (0.9050 g, 96.57% 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-d689112991714a1ab585ed413399ef69
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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