Trifluoroacetonitrile → HCID 178472209, compound

HRID 542128Notes

Reaction equation

HRID 542128 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])[CH2:2][CH3:3].[Na].[F:12][C:13]([F:17])([F:16])[C:14]#[N:15]>COCCOC>[NH2:15]/[C:14](/[C:13]([F:17])([F:16])[F:12])=[C:5](/[C:1](=[O:4])[CH2:2][CH3:3])\[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 67710TrifluoroacetonitrileHCID 78656Ethyl 3-oxovalerateHCID 5360545Sodium2×

Product 1

HCID 178472209HCID 178472209, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mechanically stirred solution of 287 g (1.99 mol) of ethyl propionylacetate in 500 ml of dry DME was added under nitrogen 8.6 g (0.348 mol) of freshly cut sodium. After all sodium had dissolved, 256 g (2.69 mol) of trifluoroacetonitrile was added over a 35 hour period. The reaction mixture was concentrated. The residue was washed with water and extracted into 500 ml of ether. The ether solution was dried and concentrated. The residue was kugelrohr distilled at 67 Pa. and then was redistilled at 67 Pa through a spinning band column. The first fraction (bp 40°-78° C.) was discarded. The next fraction (bp 79°-82° C.) was 151 g (31.6%) of product, nD25 1.4574.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe residue was washed with water
  3. extractionextracted into 500 ml of ether
  4. dry with materialThe ether solution was dried
  5. concentrationconcentrated
  6. distillationThe residue was kugelrohr distilled at 67 Pa
  7. distillationand then was redistilled at 67 Pa through a spinning band column

Sources & evidence

ORD record
ord-1252b550ae124bd5b158217c426e7714
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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