2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde → [Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-ol

HRID 1242293ノート

反応式

HRID 1242293 の反応式
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.[CH2:20]([Mg]Cl)[CH2:21][CH3:22]>C1COCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=2)[N:3]=1

参加物

4

反応物 2

HCID 219356242-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehydeHCID 178455855HCID 178455855、化合物

生成物 1

HCID 21935690[Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.600 g (2.26 mmol) of the above prepared 2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde (example 3A]) was dissolved in 11.3 ml of abs. THF and treated at −78° C. with 1.2 ml of 2M propyl magnesium chloride solution (in EtOEt, 1.06 eq.). After stirring for 15 Min. at 0° C., the reaction mixture was carefully poured onto crashed ice/NH4Cl, extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) yielded then 0.281 g of the title compound as white crystals of mp. 83–85° C.

後処理

  1. dissolutionwas dissolved in 11.3 ml of abs
  2. additionat 0° C., the reaction mixture was carefully poured
  3. extractionextracted twice with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customFlash chromatography (SiO2, hexane/AcOEt=8/2) yielded

出典と根拠

ORDレコード
ord-7f5b14c18e514cf1aa6e0f8afa7934cb
出典データセット
uspto-grants-2006_10
特許番号
US07115611B2

反応ノート

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