Hydrochloric Acid → HCID 59408360, compound

HRID 2389215Notes

Reaction equation

HRID 2389215 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)#[CH:2].[Li][CH2:25]CCC.CI.Cl>C1COCC1.O>[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([CH:12]2[CH2:13][CH2:14][CH:9]([CH:6]3[CH2:5][CH2:4][CH:3]([C:1]#[C:2][CH3:25])[CH2:8][CH2:7]3)[CH2:10][CH2:11]2)=[CH:16][CH:17]=1)[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 59408344HCID 59408344, compoundHCID 178418339Butyllithium

Product 1

HCID 59408360HCID 59408360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.5 g (11.3 mmol) of 4-ethynyl-4′-(4-propylphenyl)bicyclohexyl are initially introduced in 30 ml of THF at −20° C., and 8.6 ml (13.6 mmol) of n-BuLi (15% soln. in hexane) are added dropwise. After 1 h at this temperature, 0.85 ml (13.6 mmol) of methyl iodide is metered in, and the batch is left in the cooling bath to thaw for 3 h. Water and dil. hydrochloric acid are added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln., and the solution is dried using sodium sulfate. The crude product obtained after removal of the solvents is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1). The further purification is carried out by recrystallisation from n-heptane. This gives 4′-(4-propylphenyl)-4-prop-1-ynylbicyclohexyl as a colourless solid having an m.p. of 70° C.

Workup

  1. extractionthe mixture is extracted a number of times with MTBE
  2. washThe combined organic phases are washed with water and sat. sodium chloride soln
  3. custom, and the solution is dried

Sources & evidence

ORD record
ord-57177af2de2c40c492296c17ab160de1
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

Loading…