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

HRID 918030

반응식

HRID 918030 반응식
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

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 12788040HCID 12788040, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 344644-Ethynyl-1,1'-biphenyl수율 90.5%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-0206847ad9194784bb54ffcb6065814f
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968251

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