Water → (NZ)-4-methyl-N-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butylidene]benzenesulfinamide

HRID 2266916노트

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HRID 2266916 반응식
[F:1][C:2]([F:13])([F:12])[CH2:3][CH:4]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:5]=O.[C:14]1(C)[C:15]([S@@:20]([NH2:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.O.[CH3:25]COCC>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:25][C:18]1[CH:19]=[CH:14][C:15]([S:20](/[N:22]=[CH:5]\[CH:4]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH2:3][C:2]([F:13])([F:12])[F:1])=[O:21])=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 252317334,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)butanalHCID 68430204(s)-(+)-Toluene sulfinamide

생성물 1

HCID 87452018(NZ)-4-methyl-N-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butylidene]benzenesulfinamide수율 41.2%

시약·촉매·용매 1

HCID 76524Titanium tetraethoxide촉매

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온도
0 °C

실험 절차

To the crude organic extract of 4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butyraldehyde (prepared as in Example 26, part F, 0.6 g, 2.88 mmol) in ether (5 mL) was added titanium (IV) ethoxide (2.63 g, 11.54 mmol) followed by (S)-(+)-toluene sulfinamide (0.537 g, 3.46 mmol) and the solution was heated to reflux for 5 h. The mixture was then cooled to 0° C. and water (35 mL) was added to precipitate titanium salts. The suspension was filtered through a pad of the Celite® reagent and the filter cake was washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated to obtain a crude yellow oil (1.05 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:9 EtOAc-hexanes, to afford 4-methyl-N-[(1Z)-4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butylidene]benzenesulfinamide as a yellow oil (0.41 g, 41.2%). Mass Spectrum (−ESI): 344 (M−H)−.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux for 5 h
  3. customto precipitate titanium salts
  4. filtrationThe suspension was filtered through a pad of the Celite® reagent
  5. washthe filter cake was washed with CH2Cl2
  6. customThe layers of the filtrate were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto obtain a crude yellow oil (1.05 g)
  12. customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

출처 및 근거

ORD 기록
ord-50a50324019c40929f51c2373534c833
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858658B2

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