1,3-Propanediol → 1-(3-(1,3-Dioxan-2-yl)phenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole

HRID 2196563노트

반응식

HRID 2196563 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=[O:15])[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.[CH2:23](O)[CH2:24][CH2:25][OH:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:15]1[CH2:23][CH2:24][CH2:25][O:26][CH:14]1[C:13]1[CH:12]=[C:11]([N:10]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]([C:19]([F:20])([F:22])[F:21])=[N:9]2)[CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 598432493-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzaldehyde

생성물 1

HCID 598432051-(3-(1,3-Dioxan-2-yl)phenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole수율 79%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred solution of 122 (3.25 g, 10.62 mmol) in PhMe (53 ml) was added 1,3-propanediol (1.616 g, 21.24 mmol) followed by p-toluenesulfonic acid monohydrate (0.202 g, 1.062 mmol) and the resulting solution was allowed to stir at reflux with a Dean-Stark trap for 16 h. The solution was evaporated to dryness, and saturated NaHCO3 aqueous solution was added and the mixture was extracted with EtOAc and the extracts were dried over Na2SO4 and evaporated. The residue was purified via Biotage (5% to 40% EtOAc/Hexane; 40+M column). The title product 146 (3.04 g, 8.34 mmol, 79% yield) was obtained as an off-white solid. LRMS (ESI): (calc.) 364.3; (found) 365.2 (MH)+.

후처리

  1. temperatureat reflux with a Dean-Stark trap for 16 h
  2. customThe solution was evaporated to dryness, and saturated NaHCO3 aqueous solution
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialthe extracts were dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified via Biotage (5% to 40% EtOAc/Hexane; 40+M column)

출처 및 근거

ORD 기록
ord-57df07ce7a67448484a6d13b37f24768
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338437B2

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