Diethyl Ether → HCID 19380545, compound

HRID 2050430Notes

Reaction equation

HRID 2050430 reaction equation
[Br-].[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:43]=[CH:42][C:38]([C:39]([NH2:41])=[O:40])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1.C(OCC)C>O1CCCC1>[O:4]1[CH2:5][CH2:6][O:2][CH:3]1[CH2:7][CH:8]=[C:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:43]=[CH:42][C:38]([C:39]([NH2:41])=[O:40])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2733834Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1)HCID 153851494-(4-Oxocyclohexyl)benzamide

Product 1

HCID 19380545HCID 19380545, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

140.9 g of 2-(1,3-dioxolan-2-yl)ethyl-triphenylphosphonium bromide were suspended in 4.5 l of tetrahydrofuran while gassing with nitrogen and the suspension was treated at 0° C. within 5 minutes with 36.8 g of potassium tert.butylate. The orange suspension was stirred at room temperature for a further 1 hour and treated within 5 minutes with 46.1 g of 4-(4-oxocyclohexyl)benzamide. The reaction mixture was stirred at room temperature for a further 4.5 hours and then concentrated in a vacuum. The yellowish crystals obtained (212.5 g) were treated with 1.2 l of diethyl ether. The mixture was stirred at room temperature for 30 minutes and then suction filtered. The residue was washed with diethyl ether and then suspended in 700 ml of water. The mixture was stirred for 15 minutes and then suction filtered. The residue was washed with water and dissolved while heating in 600 ml of dioxan. The solution was left to cool to room temperature. The separated crystals were removed by filtration under suction, washed with a small amount of dioxan and hexane and dried at 60° C. in a vacuum, whereby there were obtained 39.2 g of crystalline 4-[4-[2-(1,3-dioxolan-2-yl)ethylidene]cyclohexyl]benzamide with m.p. 209°-212° C. Working-up of the mother liquor (72.6 g) gave a further 7.7 g of product and 64.2 g of a second mother liquor.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for a further 4.5 hours
  2. concentrationconcentrated in a vacuum
  3. customThe yellowish crystals obtained (212.5 g)
  4. stirringThe mixture was stirred at room temperature for 30 minutes
  5. filtrationsuction filtered
  6. washThe residue was washed with diethyl ether
  7. stirringThe mixture was stirred for 15 minutes
  8. filtrationsuction filtered
  9. washThe residue was washed with water
  10. dissolutiondissolved
  11. temperaturewhile heating in 600 ml of dioxan
  12. waitThe solution was left
  13. temperatureto cool to room temperature
  14. customThe separated crystals were removed by filtration under suction
  15. washwashed with a small amount of dioxan and hexane
  16. customdried at 60° C. in a vacuum

Sources & evidence

ORD record
ord-79b783be506f4ba18a8ce4074b86ba8b
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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