Pyridine → 1-(3,5-Bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne

HRID 1994659

反応式

HRID 1994659 の反応式
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:16]([C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)#[CH:17].C(N(CC)CC)C.N1C=CC=CC=1>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[C:2]([C:17]#[C:16][C:18]23[CH2:27][CH:22]4[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]4)[CH2:19]2)[CH2:25]3)[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=1)=[O:8]

参加物

8

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 5947811-Ethynyladamantane

生成物 1

HCID 675073001-(3,5-Bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne収率 86%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒HCID 962Water溶媒

実験手順

In a 1 L four-neck flask provided with a thermometer, a Dimroth condenser, a nitrogen inlet pipe and an agitator, 125 g of dimethyl 5-bromoisophthalate (0.458 mol), 1.1 g of triphenyl phosphine (0.00419 mol), 0.275 g of copper iodide (0.00144 mol) and 64.26 g of the obtained 1-ethynyladamantane (0.401 mol) were charged and nitrogen was passed into the flask. Then, 375 mL of dehydrated triethylamine and 200 mL of dehydrated pyridine were added therein and the mixture was agitated and dissolved. After nitrogen was passed into the flask for one hour, 0.3 g of dichlorobis (triphenyl phosphine) palladium (0.000427 mol) was quickly added and the mixture was heated and refluxed in an oil bath. Then, triethylamine and pyridine was removed under reduced pressure to obtain a brown viscous solution. The solution was added to 500 mL of water and filtered to separate a solid. The solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times and dried under pressure at 50° C., thus obtaining 121.5 g of 1-(3,5-bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne (the yield was 86%).

後処理

  1. customIn a 1 L four-neck flask provided with a thermometer
  2. dissolutiondissolved
  3. temperaturethe mixture was heated
  4. temperaturerefluxed in an oil bath
  5. customThen, triethylamine and pyridine was removed under reduced pressure
  6. customto obtain a brown viscous solution
  7. filtrationfiltered
  8. customto separate a solid
  9. washThe solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times
  10. customdried under pressure at 50° C.

出典と根拠

ORDレコード
ord-9b4587bf556b4bfcabe47e7ea5566218
出典データセット
uspto-grants-2010_01
特許番号
US07652125B2

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