Ammonia → HCID 59456350, compound

HRID 1873422Notes

Reaction equation

HRID 1873422 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([C:16]3[Se:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Li][CH2:22]CCC.CI.[Cl-].[NH4+].N>C(OCC)C>[CH3:22][C:18]1[Se:17][C:16]([CH:13]2[CH2:14][CH2:15][CH:10]([CH:7]3[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)[CH2:11][CH2:12]2)=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 59456344HCID 59456344, compoundHCID 178418339Butyllithium

Product 1

HCID 59456350HCID 59456350, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-60 °C

Procedure

2.0 g (5.9 mmol) of 2-(4′-propylbicyclohexyl-4-yl)selenophene are initially introduced in 20 ml of diethyl ether, and 5.0 ml (8.0 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 25 min and subsequently cooled to −60° C. 1.5 ml (24.1 mmol) of methyl iodide are added, and the batch is stirred for 8.5 h with slow thawing to RT. Sat. ammonium chloride soln. and conc. ammonia soln. are added successively, and the mixture is stirred vigorously for a few minutes. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water, 2 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane n-heptane:EtOAc=95:5). The further purification is carried out by recrystallisation from IPA/n-heptane (10:1) and from acetone. 2-Methyl-5-(4′-propylbicyclohexyl-4-yl)selenophene is obtained as a colourless solid (m.p. 26° C.).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 25 min
  3. additionare added successively
  4. stirringthe mixture is stirred vigorously for a few minutes
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted with MTBE
  7. washThe combined organic phases are washed with water, 2 N hydrochloric acid and sat. sodium chloride soln
  8. customThe solution is dried
  9. concentrationconcentrated to dryness
  10. customThe crude product is purified by column chromatography (SiO2, n-heptane n-heptane:EtOAc=95:5)
  11. customThe further purification
  12. customis carried out by recrystallisation from IPA/n-heptane (10:1) and from acetone

Sources & evidence

ORD record
ord-a9648d09a6534f45a9bdfabe8d7efdde
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

Loading…