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Nitrogen → Bis[4-(3-ethynylphenoxy)phenyl]methanone

HRID 344013
ノート
印刷プレビュー

反応式

HRID 344013 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=3)=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[CH3:31][C:32](O)(C#C)C.N#N.[OH-].[Na+].[CH2:41](N(CC)CC)[CH3:42]>[Pd].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C1(C)C=CC=CC=1.C(Cl)Cl>[C:31]([C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:41]#[CH:42])[CH:20]=3)=[CH:16][CH:17]=2)=[O:11])=[CH:26][CH:27]=1)#[CH:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

13

反応物 5

HCID 947NitrogenHCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22494465HCID 22494465、化合物

生成物 1

HCID 53863473Bis[4-(3-ethynylphenoxy)phenyl]methanone収率 94%

試薬・触媒・溶媒 7

HCID 11776
Triphenylphosphine
触媒
HCID 23938Palladium触媒
HCID 83717Copper iodide触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 887Methanol溶媒
HCID 1140Toluene溶媒
HCID 6344Dichloromethane溶媒

実験手順

In 20 ml of triethylamine, dissolved are 1.4 g (2.7 mmol) of 4,4'-bis(3-bromophenoxy)benzophenone and 0.67 g (8 mmol) of 2-methyl-3 -butyne-2-ol. Through this reaction mixture, N2 gas was allowed to flow for 20 min. To the resultant, 0.02 g of triphenylphosphine, 0.005 g of a palladium catalyst, i.e. (Ph3P)2PdCl2, and 0.005 g of copper iodide were added and reacted at 80° C. for 20 hours. The reaction mixture was then washed with water and subjected to extraction with methylenechloride. A intermediate reaction product was obtained by removal of the methylenechloride. To this intermediate reaction product, 20 ml of toluene, 10 ml of methanol, and 0.8 g of NaOH were added, and subsequently, the methanol and a portion of the toluene were distilled off at a temperature of 100° C. The resultant was then washed with water and subjected to extraction with methylenechloride. Finally, the extracting solvent was removed to obtain 1.3 g of 4,4'-bis(3-ethynylphenoxy) benzophenone. The yield was approximately 94%. The following is the reaction formula of this synthesis. ##STR8##

後処理

  1. customreacted at 80° C. for 20 hours
  2. washThe reaction mixture was then washed with water
  3. extractionsubjected to extraction with methylenechloride
  4. customA intermediate reaction product
  5. additionwere added
  6. distillationsubsequently, the methanol and a portion of the toluene were distilled off at a temperature of 100° C
  7. washThe resultant was then washed with water
  8. extractionsubjected to extraction with methylenechloride
  9. customFinally, the extracting solvent was removed

出典と根拠

ORDレコード
ord-42e72b750fbd43f89b312902fb70df18
出典データセット
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05864050

反応ノート

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