Nitromethane → HCID 57318775, compound

HRID 1995048Notes

Reaction equation

HRID 1995048 reaction equation
C1C[O:4]CC1.[C:6]1([CH:12]=[CH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:22]([CH3:25])([O-:24])=[O:23]>>[N+:22]([CH2:25][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](=[O:4])[CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:24])=[O:23]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 7189CinnamoylbenzeneHCID 8028Tetrahydrofuran

Product 1

HCID 57318775HCID 57318775, compoundYield 86%

Procedure

1 g of IBAF-silica (ca. 1 mmole equiv. F) is suspended in 20 ml of THF containing 6.1 g (0.1 mole) of nitromethane and 1.04 g (5 mmole) of chalcone and the resulting mixture heated with stirring. to 60° C. for 1 h. Separation (the cooled reaction mixture is filtered, the residue washed with ether and the combined filtrates evaporated to dryness) and recrystallisation of the product from ethanol gives 1.16 g (86%) of 4-nitro-1,3-diphenylbutanone, m.p. 99°-100° C. The TBAF-silica is recovered in 95% yield. The same experiment carried out at room temperature gives a 75% yield of recrystallised product and a 99% yield of recovered TBAF-silica after 6 h. On repeating the room-temperature experiment using recovered TBAF-silica, a 70% yield of recrystallised product and ca. 97% of TBAF-silica are recovered after 6 h. A control experiment carried out in which the TBAF-silica is replaced by silica along gives no detectable product (by 1H n.m.r.) after 12 h. at room temperature.

Workup

  1. temperaturethe resulting mixture heated
  2. customSeparation (
  3. customthe cooled reaction mixture
  4. filtrationis filtered
  5. washthe residue washed with ether
  6. customthe combined filtrates evaporated to dryness) and
  7. customrecrystallisation of the product from ethanol

Sources & evidence

ORD record
ord-ecbc47aac7c440f78be5e013f60a13f3
Source dataset
uspto-grants-1983_09
Patent number
US04402862

Reaction notes

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