Sodium sulfate decahydrate → HCID 117992321, compound

HRID 531017Notes

Reaction equation

HRID 531017 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:17]([O:18][CH:19]([CH3:21])[CH3:20])=[C:16]([C:22](OC)=[O:23])[CH:15]=[C:14]([CH:26]2[CH2:28][CH2:27]2)[C:13]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1.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][CH:19]([CH3:21])[CH3:20])=[C:16]([CH2:22][OH:23])[CH:15]=[C:14]([CH:26]2[CH2:28][CH2:27]2)[C:13]=1[C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 117992299HCID 117992299, compound

Product 1

HCID 117992321HCID 117992321, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutyl aluminum hydride (1.5 M toluene solution, 19.0 mL) was added at 0° C. to a mixture of methyl 2-chloro-6-cyclopropyl-4′-fluoro-3-isopropoxybiphenyl-4-carboxylate (3.45 g) and THF (40 mL), and the resultant mixture was stirred at the same temperature as above for 20 minutes in a nitrogen atmosphere. Sodium sulfate decahydrate was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and then, the solvent in the filtrate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.82 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe solvent in the filtrate was distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cd36d24fab75499693f38852b9e118a9
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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