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Pentamethyldiethylenetriamine → (4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

HRID 2105065
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HRID 2105065 반응식
[Li]CCCC.[C:6]([Si:10]([O:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH3:22])([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].CN(CCN(CCN(C)C)C)C.[CH3:35][N:36]1[C:40]([CH:41]=[O:42])=[N:39][C:38]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:37]1>C1COCC1.O>[Si:10]([O:13][C:14]1[C:15]([CH2:21][CH3:22])=[CH:16][C:17]([CH:41]([C:40]2[N:36]([CH3:35])[N:37]=[C:38]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:39]=2)[OH:42])=[C:18]([F:20])[CH:19]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]
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참가 물질

7

반응물 4

HCID 18196PentamethyldiethylenetriamineHCID 132241431-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehydeHCID 57803899Tert-butyl(2-ethyl-5-fluorophenoxy)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 57803708(4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol수율 67.5%

시약·촉매·용매

2
HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-40 °C

실험 절차

BuLi (0.67 mL, 1.6 M in hexanes, 1.1 mmol) was added dropwise to a solution of Intermediate 386.3 (250 mg, 0.98 mmol) and PMDTA (0.20 mL, 0.98 mmol) in THF (4 mL) at −78° C. The mixture was warmed to −40° C. and stirred for 30 min. After recooling the reaction to −78° C., Intermediate 386.1 (203 mg, 1.08 mmol) in THF (2 mL) was added and the mixture was warmed to ambient temperature over 2 h. Water was added to the mixture and it was extracted with EtOAc. The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 292 mg of Intermediate 386.4 as a clear oil. LCMS 442.34 (M+H).

후처리

  1. customthe reaction to −78° C.
  2. temperaturethe mixture was warmed to ambient temperature over 2 h
  3. extractionwas extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (hexanes, EtOAc)

출처 및 근거

ORD 기록
ord-5e6655e0ae8245958850c9e5e6945c7e
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576098B2

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