Ammonia → HCID 178444572, compound

HRID 2254955Notes

Reaction equation

HRID 2254955 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-(1E-pentenyl)cyclohexanone were dissolved in 8 ml of diethyl ether and 14 ml of ethanol. The solution was subsequently treated dropwise with about 70 ml of ammonia and the mixture was treated portionwise with lithium wire until the colour of the reaction mixture remained constant for 1.5 hours (about 1.3 g of lithium). Thereafter, the ammonia was evaporated off and the mixture was made acid with ammonium chloride and hydrochloric acid and left to stand for 3 days. The reaction 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 residual, yellow oil on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 1.47 g (89.1%) of trans-4-(1E-pentenyl)cyclohexanol as a light yellow, viscous oil.

Workup

  1. customThereafter, the ammonia was evaporated off
  2. waitleft
  3. waitto stand for 3 days
  4. customThe reaction 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-8bcb285b58024b05920ce6da2c149652
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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