Hydrochloric Acid → HCID 68513620, compound

HRID 1877241Notes

Reaction equation

HRID 1877241 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.O1CCCC1.Cl>O1CCCC1>[CH:19]1([CH:7]([C:6]2[CH:5]=[C:4]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:13][CH:14]=3)[S:3][C:2]=2[CH3:1])[OH:8])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86646394HCID 86646394, compoundHCID 178420632HCID 178420632, compound

Product 1

HCID 68513620HCID 68513620, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde (2.33 g) synthesized above in tetrahydrofuran (50 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (12.9 mL) at 0° C., and the mixture was stirred for 1 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane), and then purified by NH-silica gel column chromatography (ethyl acetate) to give the title compound (1.98 g, 65%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
  8. custompurified by NH-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1c21d12e755e41f6867c6d486c3dd4bd
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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