Ammonia → HCID 178444572, compound

HRID 2050460Notes

Reaction equation

HRID 2050460 reaction equation
[CH:1](/[CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].N.[Li]>C(OCC)C.C(O)C>[CH:1](/[C@H:6]1[CH2:7][CH2:8][C@H:9]([OH:12])[CH2:10][CH2:11]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 3028194Lithium2×HCID 190192404-(1E-pentenyl)cyclohexanone

Product 1

HCID 178444572HCID 178444572, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.63 g of 4-(trans-1-pentenyl)cyclohexanone were dissolved in 8 ml of diethyl ether and 14 ml of ethanol. Subsequently, the solution was treated dropwise with about 70 ml of ammonia and portionwise with lithium wire until the colour of the mixture remained constant for 1.5 hours (about 1.3 g of lithium). Thereafter, the ammonia was removed by evaporation and the mixture was made acid with ammonium chloride and hydrochloric acid and left to stand for 3 days. The mixture was then partitioned in diethyl ether/water and the aqueous phases were back-extracted with diethyl ether. The organic phases were dried over magnesium sulphate, filtered and freed from solvent on a rotary evaporator. Low-pressure chromatography of the resulting, yellow oil on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 1.47 g (89.1%) of trans-4-(trans-1-pentenyl)cyclohexanol as a light yellow, viscous oil.

Workup

  1. customThereafter, the ammonia was removed by evaporation
  2. waitleft
  3. waitto stand for 3 days
  4. customThe mixture was then partitioned in diethyl ether/water
  5. extractionthe aqueous phases were back-extracted with diethyl ether
  6. dry with materialThe organic phases were dried over magnesium sulphate
  7. filtrationfiltered
  8. customfreed from solvent on a rotary evaporator

Sources & evidence

ORD record
ord-5f8e67eaf31a4192aab310c2cc1662fd
Source dataset
uspto-grants-1991_05
Patent number
US05013478

Reaction notes

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