Sodium sulfate decahydrate → (2-Chloro-6-cyclopropyl-2',4'-difluoro-3-methoxybiphenyl-4-yl)methanol

HRID 531079Notes

Reaction equation

HRID 531079 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[C:16]([C:20](OC)=[O:21])[CH:15]=[C:14]([CH:24]2[CH2:26][CH2:25]2)[C:13]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:11][C:12]1[C:17]([O:18][CH3:19])=[C:16]([CH2:20][OH:21])[CH:15]=[C:14]([CH:24]2[CH2:26][CH2:25]2)[C:13]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700Diisobutylaluminumhydride3×HCID 117992182Methyl 2-chloro-6-cyclopropyl-2',4'-difluoro-3-methoxybiphenyl-4-carboxylate

Product 1

HCID 117992540(2-Chloro-6-cyclopropyl-2',4'-difluoro-3-methoxybiphenyl-4-yl)methanolYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminum hydride (1.5 M toluene solution, 6 mL) was added at 0° C. to a THF (40 mL) solution of methyl 2-chloro-6-cyclopropyl-2′,4′-difluoro-3-methoxybiphenyl-4-carboxylate (1.17 g), and the mixture was stirred at room temperature for 1 hour in a nitrogen atmosphere. Diisobutylaluminum hydride (1.5 M toluene solution, 2 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere. Then, diisobutylaluminum hydride (1.5 M toluene solution, 2 mL) was further added thereto, and the mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere. Sodium sulfate decahydrate was added to the reaction mixture at 0° C., and the mixture was filtered through celite. Then, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.07 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere
  2. stirringthe mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere
  3. filtrationthe mixture was filtered through celite
  4. concentrationThen, the filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a84f2274e6b74427ae0ec48602ea8a6a
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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