Citric Acid → HCID 23111762, compound

HRID 2110838Notes

Reaction equation

HRID 2110838 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[CH:13]=[O:14])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][CH:17]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 23111825HCID 23111825, compound

Product 1

HCID 23111762HCID 23111762, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(1-Benzothiophene-5-yl)benzaldehyde (3.9 g, 16.4 mmol) was dissolved in a mixed solution of ethanol (80 mL) and tetrahydrofuran (20 mL), and the mixture was ice-cooled. Sodium borohydride (0.62 g, 16.4 mmol) was added to the solution. After stirring under ice-cooling for 3 hr, aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained oil was crystallized from ethyl acetate-hexane to give the title compound (3.9 g, yield 99%) as colorless prism crystals.

Workup

  1. temperaturecooled
  2. temperaturecooling for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-67ff3aab29b8446c927c289de13f624c
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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