Methanol → HCID 86735631, compound

HRID 2083397Notes

Reaction equation

HRID 2083397 reaction equation
[CH3:1][OH:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:9]([CH2:11][O:12][N:13]=[C:14]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])#[N:10].[OH2:32].[O:33]1CCCC1>>[C:18]([OH:19])(=[O:33])/[CH:17]=[CH:16]/[C:1]([OH:32])=[O:2].[NH2:10][CH2:9][CH2:11][O:12][N:13]=[C:14]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=1)[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 867356322-[[[5-Ethoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxy]acetonitrile

Product 1

HCID 86735631HCID 86735631, compound

Procedure

24.7 Mmol (1.00 ml) of methanol and 3 ml of tetrahydrofuran (THF) were added to 7.8 mmol (0.3 g) of LiAlH4 in 10 ml of THF while stirring and cooling in ice water for 3 minutes. A solution of 1.15 mmol of 5-ethoxy-4'-trifluoromethylvalerophenone O-(cyanomethyl) oxime was then added while stirring and cooling for ten minutes. After stirring the reaction mixture at 5° C for another 3 hours it was decomposed with 1.0 ml of water. The formed hydroxides were sucked off, washed with chloroform and the filtrate was evaporated to dryness in vacuo. The resulting base was dissolved in absolute ethanol and an equimolar quantity of fumaric acid was added. The mixture was heated until a clear solution was obtained. The solvent was removed, the residue was taken up in ethanol/acetonitrile 1:1. The title compound crystallized. Melting point 150°-150.5° C.

Workup

  1. stirringwhile stirring
  2. temperaturecooling for ten minutes
  3. stirringAfter stirring the reaction mixture at 5° C for another 3 hours it
  4. washwashed with chloroform
  5. customthe filtrate was evaporated to dryness in vacuo
  6. dissolutionThe resulting base was dissolved in absolute ethanol
  7. additionan equimolar quantity of fumaric acid was added
  8. temperatureThe mixture was heated until a clear solution
  9. customwas obtained
  10. customThe solvent was removed
  11. customThe title compound crystallized

Sources & evidence

ORD record
ord-25b91dfc77cb4d4ab681e15dc32c2d4e
Source dataset
uspto-grants-1978_04
Patent number
US04085225

Reaction notes

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