Ammonium Chloride → HCID 67753893, compound

HRID 486736Notes

Reaction equation

HRID 486736 reaction equation
[Br-].[Li+].[BH4-].[Na+].[C:5]([C@H:7]1[C@H:11]([C:12](OCC)=[O:13])[S:10][CH2:9][CH2:8]1)#[N:6].[Cl-].[NH4+]>C(O)C>[C:5]([C@H:7]1[C@H:11]([CH2:12][OH:13])[S:10][CH2:9][CH2:8]1)#[N:6]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 67753650HCID 67753650, compound

Product 1

HCID 67753893HCID 67753893, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under nitrogen atmosphere, lithium bromide (208 mg) and sodium borohydride (50 mg) were dissolved in ethanol (3 ml) and the mixture was stirred for 45 minutes at room temperature. Under ice-cooling, trans-4-cyano-5-ethoxycarbonyltetrahydrothiophene (122 mg) dissolved in ethanol (2 ml) was added to the solution and the mixture was stirred over night. Aqueous ammonium chloride solution was added to the mixture under ice-cooling and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 90 mg (95%) of trans-4-cyano-5-hydroxymethyltetrahydrothiophene.

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added to the solution
  3. stirringthe mixture was stirred over night
  4. temperaturecooling
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-cd856843125845f4a9c745057e979493
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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