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

HRID 404338Notes

Reaction equation

HRID 404338 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].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>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 3

HCID 8028TetrahydrofuranHCID 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 96.57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of T9.3 (1.1530 g, 3.079 mmol) and 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 T9.4 (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
  6. customto provide T9.4 (0.9050 g, 96.57% yield)

Sources & evidence

ORD record
ord-e56b53a30aa14111a1d15f32871f33a0
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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