Tetrahydrofuran → HCID 19862725, compound

HRID 1721963Notes

Reaction equation

HRID 1721963 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]#[CH:21].C1COCC1>[Cu]I.CCOCC>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]#[C:21][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 112773071-(4-iodophenyl)pyrrolidineHCID 198626861-Bromo-4-[(prop-2-yn-1-yl)oxy]butane

Product 1

HCID 19862725HCID 19862725, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(4-iodophenyl)pyrrolidine (22.8 g), the product of stage (i) (16.0 g), BTPC (1.5 g) and copper (I) iodide (150 mg) in DEA (125 ml) and THF (125 ml) was stirred under nitrogen for 18 h. The dark mixture was treated with ether (250 ml), the precipitate was removed by filtration and the filtrate was concentrated to a black oil which was purified by FCC (hexane→System D 9:1) to give the title compound as a pale yellow oil (3.0 g) T.l.c. (System D 9:1) Rf 0.24.

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated to a black oil which
  3. customwas purified by FCC (hexane→System D 9:1)

Sources & evidence

ORD record
ord-d4e004abed024b77b4f9310887391b76
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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