Hydrochloric Acid → HCID 61088367, compound

HRID 2090975Notes

Reaction equation

HRID 2090975 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]=[O:11])=[CH:2]1.O1CCCC1.[CH:17]1([Mg]Br)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[OH:11])=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2273281-Benzothiophene-3-carbaldehydeHCID 178420632HCID 178420632, compound

Product 1

HCID 61088367HCID 61088367, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (40 mL) of 1-benzothiophene-3-carbaldehyde (2.25 g) in tetrahydrofuran was added dropwise 1.0M cyclohexylmagnesium bromide tetrahydrofuran solution (20.9 mL) at 0° C., and the mixture was stirred for 1.5 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 (ethyl acetate:hexane=3:17, volume ratio) to give the title object compound (2.37 g, 69%) as an orange oil.

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 (ethyl acetate:hexane=3:17, volume ratio)

Sources & evidence

ORD record
ord-ad62c5410a694cd88459829f9d943e60
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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