Aluminium lithium hydride → (4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methanol

HRID 1662530Notes

Reaction equation

HRID 1662530 reaction equation
[CH3:1][C:2]([Si:5]([CH3:28])([CH3:27])[O:6][CH2:7][C:8]1[CH:9]=[C:10]([C:23](OC)=[O:24])[C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:12][CH:13]=1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][C:2]([Si:5]([CH3:27])([CH3:28])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH2:23][OH:24])[CH:9]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57706632Methyl 4-((((1,1-dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carboxylate

Product 1

HCID 57706179(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methanolYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round bottom flask was charged with 83.18A (0.82 g, 2.0 mmol) and THF (10 mL). To the solution was added LAH (1.0 M in THF) (available from Aldrich) (2.0 mL, 2.0 mmol) dropwise at room temperature. The mixture was stirred for 10 minutes, quenched with aqueous Rochelle salt, and diluted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-25% EtOAc/hexane) to afford 83.18B (0.73 g, 96% yield) as a colorless oil.

Workup

  1. customquenched with aqueous Rochelle salt
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash chromatography (0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-eb5b75f2e8ea4d70aebe9b714c36b9cf
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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