Hydrochloric Acid → HCID 23016498, compound

HRID 417818Notes

Reaction equation

HRID 417818 reaction equation
C([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:20]=[CH:19][C:10]2[O:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[O:14][C:9]=2[C:8]=1[CH3:21].[CH2:22]([O:24]CC)C.Cl>O>[F:17][C:12]1([F:18])[O:11][C:10]2[CH:19]=[CH:20][C:7]([CH:22]([OH:24])[CH:3]([CH3:2])[CH3:4])=[C:8]([CH3:21])[C:9]=2[O:14][C:13]1([F:16])[F:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 23016515HCID 23016515, compoundHCID 178418339Butyllithium

Product 1

HCID 23016498HCID 23016498, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 7.8 ml of n-butyllithium (1.57 M-n-hexane solution) was dropwise added at −50° C. to a mixture comprising 3.36 g of 6-bromo-2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxane and 40.6 ml of ethyl ether, and then the mixture was stirred at the same temperature for 30 minutes. 0.89 g of isobutylaldehyde was dropwise added thereto at a temperature of at most −70° C., and the temperature was raised to room temperature followed by a reaction for 15 hours. After completion of the reaction, the reaction mixture was put into water, and then weakly acidified by an addition of hydrochloric acid. Then the mixture was extracted with ether, and the extract was washed with water and dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain 1.90 g of oily 1-(2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxan-6-yl)-2-methylpropanol. The NMR spectrum data of this product were as follows.

Workup

  1. customfollowed by a reaction for 15 hours
  2. customAfter completion of the reaction
  3. extractionThen the mixture was extracted with ether
  4. washthe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-bcb2ee7257544f51b9b2dc0d3c14bacf
Source dataset
uspto-grants-2012_01
Patent number
US08093241B2

Reaction notes

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