Water → (E)-N-ethyl-N-(2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

HRID 1756174

Reaction equation

HRID 1756174 reaction equation
[CH2:1]([N:3]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:20]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][Si](C)(C)C)[CH3:2].C(OCC)(=O)C.O>CO.O1CCCC1.[F-].[K+]>[CH2:1]([N:3]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:20]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[CH:8])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 19917013(E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

Product 1

HCID 19917041(E)-N-ethyl-N-(2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamineYield 78.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 522689Potassium FluorideSolvent

Procedure

2.0 g of the resulting allylamine compound was dissolved in a mixture of methanol (5 ml) and tetrahydrofuran (5 ml), and 10 ml of a saturated aqueous solution of potassium fluoride was added. The mixture was stirred overnight at room temperature, and then ethyl acetate and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [methylene chloride/methanol=100/1] to give 1.3 g of (E)-N-ethyl-N-(2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine as a colorless oil.

Workup

  1. additionwas added
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [methylene chloride/methanol=100/1]

Sources & evidence

ORD record
ord-d22b8a90a9b6490289afc8a4116b7dcf
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Linked notes

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