Tetrahydrofuran → HCID 57705690, compound

HRID 404343Notes

Reaction equation

HRID 404343 reaction equation
[CH3:1][C:2]1([CH3:27])[C:7]([C:8]2[CH:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:6][CH2:5][CH2:4][CH2:3]1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[CH3:1][C:2]1([CH3:27])[C:7]([C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706936[1,1′-Biphenyl]-4-carboxylic acid, 2-(6,6-dimethyl-1-cyclohexen-1-yl)-2′-fluoro-5′-methoxy-, methyl ester

Product 1

HCID 57705690HCID 57705690, compoundYield 90.2%

Procedure

To a stirred solution of T12.6 (0.300 g, 0.814 mmol) in THF (0.0587 g, 0.814 mmol) at 0° C. was added LAH (1.63 mL, 1.63 mmol, 1.0M). The resulting mixture was stirred for 4.5 hours. Next, 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-20% EtOAc in hexanes) to yield T12.7 as a colorless oil (0.250 g, 90.2% yield).

Workup

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

Sources & evidence

ORD record
ord-46f2613607444e85898d59f55596133d
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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