Citric Acid → HCID 23111762, compound

HRID 1163296Notes

Reaction equation

HRID 1163296 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-Benzothien-5-yl)benzaldehyde (3.9 g, 16.4 mmol) was dissolved in ethanol (80 mL) and tetrahydrofuran (20 mL), and the mixture was ice-cooled. Sodium borohydride (0.62 g, 16.4 mmol) was added to this solution, and the mixture was stirred 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 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 magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9edd0ef982d947798e13a6421068cfa4
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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