Potassium Carbonate → (R)-5-trifluoromethyl-2-(2,3-epoxypropoxy)benzaldehyde

HRID 369077노트

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HRID 369077 반응식
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:14][CH2:13]2)(=O)=O)=CC=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([CH:25]=1)[CH:23]=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[F:16][C:17]([F:27])([F:28])[C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:11][C@@H:12]2[O:14][CH2:13]2)=[C:22]([CH:25]=1)[CH:23]=[O:24]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 155009882-Hydroxy-5-trifluoromethylbenzaldehyde

생성물 1

HCID 53892129(R)-5-trifluoromethyl-2-(2,3-epoxypropoxy)benzaldehyde수율 72.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
60 °C

실험 절차

A mixture of (R)-glycidyl 4-toluenesulphonate (24 g), 5-trifluoromethyl-2-hydroxybenzaldehyde (20 g) and potassium carbonate (16 g) in dimethylformamide (550 ml) was stirred and heated at 60° C. for 72 hours. After cooling, brine (1.5 L) was added and the resultant mixture extracted with ether (4×500 ml). The combined ether extracts were washed with brine (2×500 ml), then water (500 ml) and dried over magnesium sulphate. The residue was purified by flash column chromatography on silica eluting with a 3:1 mixture of petroleum ether (b.p. 40-60 ° C.) and ethyl acetate to give (R)-5-trifluoromethyl-2-(2,3-epoxypropoxy)benzaldehyde (18.7 g) as a yellow oil.

후처리

  1. temperatureAfter cooling
  2. extractionthe resultant mixture extracted with ether (4×500 ml)
  3. washThe combined ether extracts were washed with brine (2×500 ml)
  4. dry with materialwater (500 ml) and dried over magnesium sulphate
  5. customThe residue was purified by flash column chromatography on silica eluting with a 3:1 mixture of petroleum ether (b.p. 40-60 ° C.) and ethyl acetate

출처 및 근거

ORD 기록
ord-c62a18a3333d4ff6aa2cee95149e7f62
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136825

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