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Tetrahydrofuran → (2'-Fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-yl) methanol

HRID 404359
Notes
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Reaction equation

HRID 404359 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[CH2:20][CH:21]([CH3:23])[CH3:22].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[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[CH2:20][CH:21]([CH3:23])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706197Methyl 2'-fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706573(2'-Fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-yl) methanolYield 100.2%

Procedure

To a stirred solution of T23.5 (0.293 g, 0.9 mmol) in THF (5 mL, 0.9 mmol) at 0° C. was added LAH in THF (2 mL, 2 mmol, 1.0M). The reaction was stirred for one hour and then 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield T23.6 as a colorless oil (0.260 g, 97% yield).

Workup

  1. customto quench the mixture
  2. extractionThe reaction was extracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-81de502019574c088600ba41a4418d15
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748462B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes