Dimethyl Sulfoxide → 4-Ethynyl-1,1'-biphenyl

HRID 918030

反応式

HRID 918030 の反応式
CC(C)([O-])C.[K+].CS(C)=O.Br[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:13]Br>C(O)(C)(C)C>[CH:13]#[C:12][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 12788040HCID 12788040、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 344644-Ethynyl-1,1'-biphenyl収率 90.5%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of 26 g of potassium t-butoxide in 400 ml of a 1:1 mixture (v/v) of dimethyl sulfoxide and t-butanol at 10°-15° was added with stirring a solution of 39 g of 4-(1,2-dibromoethyl)biphenyl in 400 ml of the same solvent mixture. After stirring for 20 minutes, the reaction mixture was poured into ice-water. The resulting mixture was extracted with diethyl ether. The diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water, and dried over anhydrous sodium sulfate. The diethyl ether was distilled under reduced pressure and the solid residue crystallized from aqueous ethanol to give 18.5 g of crude 4-biphenylacetylene, mp 79°-81°. Two recrystallizations from hexane gave pure 4-biphenylacetylene, mp 82°-85°. The following elemental analysis was obtained:

後処理

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. washThe diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe diethyl ether was distilled under reduced pressure
  5. customthe solid residue crystallized from aqueous ethanol

出典と根拠

ORDレコード
ord-0206847ad9194784bb54ffcb6065814f
出典データセット
uspto-grants-1976_07
特許番号
US03968251

関連ノート

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