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

HRID 251717

反応式

HRID 251717 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>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>[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

7

反応物 3

HCID 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 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

Next, 125 g of dimethyl 5-bromoisophthalate (458 mmol), 1.1 g of triphenylphosphine (4.19 mmol), 0.275 g of copper iodide (1.44 mmol), 64.26 g of 1-ethynyladamantane (401 mmol), 375 mL of dehydrated triethylamine, 200 mL of dehydrated pyridine, 0.3 g of dichlorobis (triphenylphosphine) palladium (0.427 mmol) and a stirrer were charged in a 1 L recovery flask and agitated at 100° C. for one hour. After reaction solution was filtered, solvent was removed from the reaction solution under reduced pressure. Solid thus obtained was washed with 1 L of ion-exchange water and then with 1 L of 2 mol/L hydrochloric acid aqueous solution, followed by drying under reduced pressure, thus obtaining 121.5 g of 1-(3,5-bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne (344.9 mmol; yield: 86.0%).

後処理

  1. customAfter reaction solution
  2. filtrationwas filtered
  3. customsolvent was removed from the reaction solution under reduced pressure
  4. customSolid thus obtained
  5. washwas washed with 1 L of ion-exchange water
  6. customby drying under reduced pressure

出典と根拠

ORDレコード
ord-b9a4d450389741cb93667582ae56426d
出典データセット
uspto-grants-2011_01
特許番号
US07863347B2

関連ノート

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