Diethyl Ether → 2-(p-Biphenylyl)-3,4-pentadien-2-ol

HRID 437924

反応式

HRID 437924 の反応式
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:15])([C:9]#[C:10][CH2:11]N(C)C)[CH3:8].[OH-].[Na+].C(OCC)C>O1CCCC1.C1C=CC=CC=1.CCCCC>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:15])([CH:9]=[C:10]=[CH2:11])[CH3:8]

参加物

7

反応物 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 706246472-(p-Biphenylyl)-5-dimethylamino-3-pentyn-2-ol

生成物 1

HCID 867348952-(p-Biphenylyl)-3,4-pentadien-2-ol

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 8003Pentane溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 507 g of the crude (foam) methiodide of 2-(p-biphenylyl)-5-dimethylamino-3-pentyn-2-ol obtained by step (b) above, in 4 liters of dry tetrahydrofuran, is added dropwise over a period of one hour, with cooling (to keep at room temperature), 478 g of a solution of sodium dihydrobis (2-methoxyethoxy) aluminate 70% w/w in benzene in 800 ml of dry tetrahydrofuran. The resulting mixture is then stirred at room temperature for 2 hours. The mixture is then cooled to 10° and dropwise there is added 3 liters of 2N sodium hydroxide, with stirring and cooling to 10° to 20°. 10 liters of diethyl ether are then added, in one portion, to the mixture. Solids present (inorganic salts) are removed by filtration on Celite. The filtrate is then extracted twice with 5 liter portions of water, the water washes then being washed three times with 5 liters of diethyl ether each time. The combined ether phases are washed once with 3 liters of aqueous saturated brine solution. The combined organic phases are dried over sodium sulfate, filtered, and the filtrate evaporated by rotary evaporation at 40° to obtain the crude product as an oil. The oil is taken up in 7 liters pentane (heated) and then the resulting pentane solution chilled until a precipitate forms. The precipitate is collected by filtration and washed with pentane. The precipitate is crystallized from pentane five times, then dried in a vacuum oven at room temperature for 12 hours to yield the title product, m.p. 65°-66°.

後処理

  1. additionis added dropwise over a period of one hour
  2. temperatureThe mixture is then cooled to 10°
  3. stirringwith stirring
  4. temperaturecooling to 10° to 20°
  5. customSolids present (inorganic salts) are removed by filtration on Celite
  6. extractionThe filtrate is then extracted twice with 5 liter portions of water
  7. washthe water washes then being washed three times with 5 liters of diethyl ether each time
  8. washThe combined ether phases are washed once with 3 liters of aqueous saturated brine solution
  9. dry with materialThe combined organic phases are dried over sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated by rotary evaporation at 40°
  12. customto obtain the crude product as an oil
  13. filtrationThe precipitate is collected by filtration
  14. washwashed with pentane
  15. customThe precipitate is crystallized from pentane five times
  16. customdried in a vacuum oven at room temperature for 12 hours

出典と根拠

ORDレコード
ord-fcf1c0416dc54deb8d1655105a9a732b
出典データセット
uspto-grants-1977_06
特許番号
US04032580

関連ノート

読み込み中…