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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
ノート
印刷プレビュー

反応式

HRID 2105065 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5e6655e0ae8245958850c9e5e6945c7e
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576098B2

反応ノート

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