1-Ethynylcyclohexanol → HCID 15453738, compound

HRID 1700275Notes

Reaction equation

HRID 1700275 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1.C(N(CC)CC)C.[C:18]([C:20]1(Cl)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)#[CH:19].C(C1(O)CCCCC1)#C>CCOCC.O.CCOCC.Cl[Cu]>[CH2:2]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:20]2([C:18]#[CH:19])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][CH:5]=1)[CH3:1]

Participants

8

Reactant 4

HCID 65251-EthynylcyclohexanolHCID 8471TriethylamineHCID 90764-EthoxyanilineHCID 201548Cyclohexane, 1-chloro-1-ethynyl-

Product 1

HCID 15453738HCID 15453738, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolventHCID 21584184Diethylether waterSolvent

Procedure

To a solution, cooled to 10° C., of 18.2 mmol (2.5 g) of p-phenetidine in a mixture of ether:water (4:1; 30 ml) containing 24.5 mmol (3.42 ml) of triethylamine there are added, in succession, 0.25 mmol (0.025 g) of CuCl, 0.39 mmol (0.025 g) of Cu and, dropwise, 28.0 mmol (4.0 g) of 1-ethynyl-1-chlorocyclohexane prepared according to the method described in J. Am. Chem. Soc., 83, 725, 1961, starting from 1-ethynylcyclohexanol. After stirring for 4 hours (allowing the temperature to increase towards ambient temperature) the reaction mixture is diluted with ether and then washed with 1N sulphuric acid solution. The ethereal phase is removed and the aqueous phase is neutralised (at 0° C.) using potassium hydroxide pellets and then re-extracted with ether. The organic phase is dried and then concentrated to yield the expected product.

Workup

  1. washwashed with 1N sulphuric acid solution
  2. customThe ethereal phase is removed
  3. custom(at 0° C.)
  4. extractionre-extracted with ether
  5. customThe organic phase is dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-885bc0f80a1e4ff499e0016deb2e854e
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

Loading…