Ethyl Acetate → HCID 53904180, compound

HRID 1195382Notes

Reaction equation

HRID 1195382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH:10]=O)=[CH:4][CH:3]=1.C1(P(=CC=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O:50][CH2:51][CH3:52])(=O)C.[Br-].[Li+]>C1(C)C=CC=CC=1.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:9]([C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)[CH:10]=[CH:52][CH:51]=[O:50])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 82050Lithium BromideHCID 14539527HCID 14539527, compound

Product 1

HCID 53904180HCID 53904180, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 448 g (1.37 mol) of 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal and 445 g (1.46 mol) of triphenylphosphoranylidene acetaldehyde in 5.5 L of toluene was heated with stirring to 55° C. After turning off the heat source, the temperature rose to 62° C. After 20 minutes, heat was applied and 60° C. was maintained for 30 minutes. Analytical TLC indicated that the reaction was complete (50% ethyl acetate in hexane). Lithium bromide (128 g, 1.47 mol) was added and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in 900 mL of boiling absolute ethanol. To this solution was slowly added 900 mL of hexane. After 16 hours at ambient temperature and 2 hours at cold freezer temperature, the mixture was filtered to give 418 g (86.6%) of the title compound; m.p.=161°-165° C.

Workup

  1. temperaturewas heated
  2. customrose to 62° C
  3. temperatureheat
  4. customwas applied and 60° C.
  5. temperaturewas maintained for 30 minutes
  6. stirringthe mixture was stirred at 60° C. for 1 hour
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in 900 mL
  10. waitAfter 16 hours at ambient temperature
  11. filtration2 hours at cold freezer temperature, the mixture was filtered

Sources & evidence

ORD record
ord-2a38faab18f841108104a08b18c74b72
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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