Dimethyl Sulfoxide → 1-(4-Methoxybenzo[d]oxazol-2-yl)ethanone

HRID 275801

반응식

HRID 275801 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:17]=2[N:18]=1)[CH3:13].C(N(CC)CC)C>ClCCl.O>[C:12]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:17]=2[N:18]=1)(=[O:11])[CH3:13]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 183166442-(1-Hydroxyethyl)-4-methoxybenzoxazole

생성물 1

HCID 183166331-(4-Methoxybenzo[d]oxazol-2-yl)ethanone수율 70.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

A solution of oxalyl chloride (0.25 ml) in dichloromethane (6.5 ml) was cooled to −55° C. under nitrogen. A solution of dimethylsulphoxide (0.44 ml) in dichloromethane (1.3 ml) was added dropwise, and the mixture stirred for 5 minutes at −55° C. before addition of a solution of 2-(1-hydroxyethyl)-4-methoxybenzoxazole (0.5 g) in dichloromethane (2.5 ml). Stirring was continued for 15 minutes at −55° C., then triethylamine (1.8 ml) was added. The mixture was stirred at −55° C. for 5 minutes and was then allowed to warm to room temperature. It was poured into water (25 ml) and the layers separated. The aqueous phase was extracted with dichloromethane (20 ml). The combined organic phases were dried over magnesium sulphate, evaporated in vacuo and purified by flash chromatography eluting with 30% ethyl acetate in hexane to yield the title compound as a white solid (350 mg).

후처리

  1. stirringThe mixture was stirred at −55° C. for 5 minutes
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with dichloromethane (20 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customevaporated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-a6454b6dd1f1472880a7a3fbc8b90035
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353010B1

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