Ethanol → HCID 54225068, compound

HRID 1200052Notes

Reaction equation

HRID 1200052 reaction equation
[BH4-].[Na+].C(O)C.[S:6]1[CH:10]=[C:9]([CH:11]=[CH:12][C:13]2[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=2)[C:8]2[CH:20]=[CH:21][CH:22]=[CH:23][C:7]1=2>O>[OH:19][CH2:18][C:16]1[S:17][C:13]([CH:12]=[CH:11][C:9]2[C:8]3[CH:20]=[CH:21][CH:22]=[CH:23][C:7]=3[S:6][CH:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 537352685-[2-(Benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxaldehyde

Product 1

HCID 54225068HCID 54225068, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred, chilled (0° C.) suspension of sodium borohydride (0.50 g) and absolute ethanol (250 ml), under nitrogen, was treated in portions with 5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxaldehyde (3.0 g). After stirring at room temperature overnight, the mixture was poured into water (250 ml). The organic phase was removed in vacuo, and the resulting aqueous phase was extracted with dichloromethane. The combined, dried over anhydrous magnesium sulfate, filtered organic phase was evaporated. The residue was purified by high performance liquid chromatography (silica gel, loaded and eluted first with dichloromethane, then with ethyl acetate). The appropriate fractions were combined and evaporated. The residue was recrystallized from toluene/hexane to yield 2.15 g (71%) of product, mp 68°-70° C.

Workup

  1. temperatureA stirred, chilled
  2. customThe organic phase was removed in vacuo
  3. extractionthe resulting aqueous phase was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered organic phase
  6. customwas evaporated
  7. customThe residue was purified by high performance liquid chromatography (silica gel
  8. washloaded and eluted first with dichloromethane
  9. customevaporated
  10. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-6494c46d63f1486894084b40a77f11cc
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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