Sodium borohydride → HCID 12838411, compound

HRID 1156541Notes

Reaction equation

HRID 1156541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:16][C:17]#[N:18])[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:16][C:17]#[N:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[OH:15])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12838410[1-(3-Methoxyphenyl)-2-oxocyclohexyl]acetonitrile2×

Product 1

HCID 12838411HCID 12838411, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

243 g of 1-(m-methoxyphenyl)-2-oxo-cyclohexane-1-acetonitrile are dissolved in 2.5 liters of ethanol, whereupon a total of 25 g of sodium borohydride is added portionwise while stirring. The temperature rises to about 45° C. After 1 hour, 1-(m-methoxyphenyl)-2-oxo-cyclohexane-1-acetonitrile can no longer be detected by thin-layer chromatography. After distillation of the solvent, the residue is treated with 500 ml of ice water and extracted twice with 1.5 liters of ether each time. The combined extracts are washed once in succession with 0.5 liter of water, 0.5 liter of 1 N hydrochloric acid and 0.5 liter of water, dried over magnesium sulfate, and the solvent is removed by distillation, whereby there are obtained 240 g of 1-(m-methoxyphenyl)-2-hydroxy-cyclohexane-1-acetonitrile in the form of a colorless, viscous oil which is dissolved without purification in 2 liters of pyridine and treated with 130 ml of phosphorus oxychloride. The mixture is boiled at reflux for 3 hours and subsequently evaporated in a water-jet vacuum. The residue is treated with water while cooling with ice and extracted twice with 1.5 liters of ether each time, whereupon the ethereal phases are combined, washed once in succession with 0.5 liter of water and 0.5 liter of 1 N hydrochloric acid and subsequently twice with water, dried over magnesium sulfate and evaporated. The brown oil obtained is purified on a 10-fold amount of silica gel. After elution of the impurities with about 10 liters of ether/petroleum ether (1:9), 1-(m-methoxyphenyl)-2-cyclohexene-1-acetonitrile is eluted with about 10 liters of ether/petroleum ether (1:3). The fractions which are uniform in accordance with thin-layer chromatography are combined, and the solvent is removed by distillation and the product remains behind as a light yellow oil.

Workup

  1. additionis added portionwise
  2. customrises to about 45° C
  3. distillationAfter distillation of the solvent
  4. additionthe residue is treated with 500 ml of ice water
  5. extractionextracted twice with 1.5 liters of ether each time
  6. washThe combined extracts are washed once in succession with 0.5 liter of water, 0.5 liter of 1 N hydrochloric acid and 0.5 liter of water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent is removed by distillation, whereby there

Sources & evidence

ORD record
ord-06c1f7cc7c434e33af1043c6859c105b
Source dataset
uspto-grants-1982_06
Patent number
US04336268

Reaction notes

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