Hydrochloric Acid → HCID 68511971, compound

HRID 1877236Notes

Reaction equation

HRID 1877236 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.O1CCCC1.Cl>O1CCCC1>[CH:15]1([CH:7]([C:6]2[CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:3][C:2]=2[CH3:1])[OH:8])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10910588HCID 10910588, compoundHCID 178420632HCID 178420632, compound2×

Product 1

HCID 68511971HCID 68511971, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-5-phenylthiophene-3-carbaldehyde (1.72 g) synthesized above in tetrahydrofuran (40 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (12.8 mL) at 0° C., and the mixture was stirred for 2 hr. 1.0M Cyclohexylmagnesium bromide-tetrahydrofuran solution (5 mL) was added dropwise again, and the mixture was further stirred at 0° C. for 1 hr. 1N Hydrochloric acid was added to quench the reaction, tetrahydrofuran was evaporated using evaporator, 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 (20% ethyl acetate/hexane) to give the title compound (2.33 g, 96%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was further stirred at 0° C. for 1 hr
  2. customto quench
  3. customthe reaction, tetrahydrofuran
  4. customwas evaporated
  5. customevaporator
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4307c2b36b4a4dbd999aa6597e351d60
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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