Tetrahydrofuran → HCID 90423191, compound

HRID 531064Notes

Reaction equation

HRID 531064 reaction equation
C1COCC1.[CH:6]1([C:9]2[CH:14]=[C:13]([C:15](OCC)=[O:16])[CH:12]=[C:11]([O:20][CH:21]([CH3:23])[CH3:22])[C:10]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH:6]1([C:9]2[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[C:11]([O:20][CH:21]([CH3:23])[CH3:22])[C:10]=2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117992144HCID 117992144, compound

Product 1

HCID 90423191HCID 90423191, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A THF (10 mL) solution of ethyl 2-cyclopropyl-4′-fluoro-6-isopropoxybiphenyl-4-carboxylate (1.22 g) was added to a THF (20 mL) suspension of lithium aluminum hydride (0.3 g) under ice cooling in a nitrogen atmosphere. After stirring at the same temperature as above for 30 minutes, water (0.3 mL) and a 15% aqueous sodium hydroxide solution (0.3 mL) were added thereto, and the mixture was stirred for 5 minutes. Water (0.9 mL) was further added to the reaction mixture, and the mixture was stirred for 30 minutes and then filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate). Manganese dioxide (3.21 g) was added to a toluene (10 mL) solution of the obtained purified product, and the mixture was stirred at 70° C. for 30 minutes in a nitrogen atmosphere. The reaction mixture was filtered, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (850 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  5. additionManganese dioxide (3.21 g) was added to a toluene (10 mL) solution of the obtained
  6. custompurified product
  7. stirringthe mixture was stirred at 70° C. for 30 minutes in a nitrogen atmosphere
  8. filtrationThe reaction mixture was filtered
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aab8c8585b5f4d7b95b7de3cc455bbe3
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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