Sodium hydride → 8-Trifluoroacetamido-1-octyne

HRID 1386650Notes

Reaction equation

HRID 1386650 reaction equation
[H-].[Na+].[F:3][C:4]([F:9])([F:8])[C:5]([NH2:7])=[O:6].I[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18].[Cl-].[NH4+]>CN(C=O)C.CCOCC>[F:3][C:4]([F:9])([F:8])[C:5]([NH:7][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]#[CH:11])=[O:6]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67717TrifluoroacetamideHCID 226215568-Iodo-1-octyne

Product 1

HCID 226215548-Trifluoroacetamido-1-octyneYield 79.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium hydride (60% oil, 9.82 g, 245 mmol) in DMF (200 ml), trifluoroacetamide (34.7 g, 307 mmol) divided into 10 portion was added portionwise with ice cooling. Then, the reaction mixture was added with a solution of 8-iodo-1-octyne (14.5 g, 61.4 mmol) in DMF (60 ml), and stirred at room temperature for two hours. The reaction mixture was added with saturated aqueous ammonium chloride (400 ml) and ether (400 ml) for extraction. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent), and crystallized from hexane to afford 10.8 g of 8-trifluoroacetamido-1-octyne (yield; 79.3%). Melting point: 29.5-30.0° C.

Workup

  1. additionwas added portionwise with ice cooling
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent)
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-779f1d6c92b447cba0925574dee08ed4
Source dataset
uspto-grants-2001_07
Patent number
US06265569B1

Reaction notes

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