Diethyl Ether → HCID 19380545、化合物

HRID 484271ノート

反応式

HRID 484271 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 19380545HCID 19380545、化合物収率 61.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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-(4oxocyclohexyl)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 fried at 60° C. in a vacuum, whereby there were obtained 39.2 g of crystalline 4-[4-[2(-1,3-dioxolan-2-yl)ethylidene]cyclo-hexyl]benzamide with m.p. 209°-212° C. Working-up of the mother liquor (72.6 g) gave a further 7.7 g of produce and 64.2 g of a second mother liquor.

後処理

  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 and fried at 60° C. in a vacuum

出典と根拠

ORDレコード
ord-9bba2d816b624f3b9c64590a1450c0eb
出典データセット
uspto-grants-1993_07
特許番号
US05230826

反応ノート

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