Dimethyl Sulfoxide → 4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde

HRID 860585노트

반응식

HRID 860585 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[O:16][C:17]=1[CH2:18][OH:19])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[O:16][C:17]=1[CH:18]=[O:19])[CH3:12]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58765785[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol

생성물 1

HCID 587657044-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of oxalyl chloride (2.0M/DCM, 3.52 mL, 7.04 mmloe) in DCM (50 mL), is injected DMSO (0.998 mL, 14.1 mmole) and stirred for 15 minute at −78° C. A solution of [4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol (1.59 g, 5.86 mmole) in DCM (10 mL) is then added. After stirred for 30 minutes, triethyl amine (4.08 mL, 29.3 mmole) is added. The reaction is kept at −78° C. for another 30 minutes, then warmed up to room temperature for 2 hours, washed with brine (3×50 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, 10% ethyl acetate in hexane) and concentrated to provide the titled compound as a white solid. Mass [EI+] 270 (M+H)+.

후처리

  1. stirringAfter stirred for 30 minutes
  2. waitThe reaction is kept at −78° C. for another 30 minutes
  3. temperaturewarmed up to room temperature for 2 hours
  4. washwashed with brine (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by flash chromatography (silica gel, 10% ethyl acetate in hexane)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-77c4c0035ae74717bfa6aff3702bb290
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153878B2

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