Ethanol → HCID 178450566, compound

HRID 542139Notes

Reaction equation

HRID 542139 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[Na+].C(O)C.[F:20][C:21]([F:25])([F:24])[C:22]#[N:23]>O>[C:1]([C:6](=[C:22]([NH2:23])[C:21]([F:25])([F:24])[F:20])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 67710TrifluoroacetonitrileHCID 238498Ethyl 3-oxohexanoateHCID 517045Sodium Acetate

Product 1

HCID 178450566HCID 178450566, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mechanically stirred mixture of 100 g (0.632 mol) of ethyl butyrylacetate, 52 g of sodium acetate, 100 ml of ethanol and 100 ml of water at 70° C. was passed 63 g of trifluoroacetonitrile in 1 day. The reaction mixture was poured into ice water. The oil precipitate was extracted into ether. The ether solution was dried and concentrated. The residue was kugelrohr distilled at 133 Pa (pot temperature 70°-110° C.). The distillate was further distilled through a Vigreaux column at 106 Pa to give 90.9 g (36.3%) of product, bp 90°-97° C., nD25 1.4585.

Workup

  1. customin 1 day
  2. extractionThe oil precipitate was extracted into ether
  3. dry with materialThe ether solution was dried
  4. concentrationconcentrated
  5. distillationThe residue was kugelrohr distilled at 133 Pa (pot temperature 70°-110° C.)
  6. distillationThe distillate was further distilled through a Vigreaux column at 106 Pa

Sources & evidence

ORD record
ord-789e45334017488cb9a5ccb0507b962d
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

Loading…