Acetone → 3-Fluoro-α,α-dimethyl-4-pyridinemethanol

HRID 2368670ノート

反応式

HRID 2368670 の反応式
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li+].CC([N-]C(C)C)C.[CH3:16][C:17]([CH3:19])=[O:18]>C1COCC1>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:17]([OH:18])([CH3:19])[CH3:16]

参加物

5

反応物 3

HCID 180AcetoneHCID 677943-FluoropyridineHCID 2724682Lithium diisopropylamide

生成物 1

HCID 131295773-Fluoro-α,α-dimethyl-4-pyridinemethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-Fluoropyridine (11.0 g, 113.0 mmol) in 100 mL of THF was treated with LDA (1.5M, 100.0 mL, 150.0 mmol) at −78° C. for 50 min under argon. Acetone (28 mL) was added and the resulting reaction mixture was stirred at −78° C. to −40° C. for 50 min. The reaction was then quenched with aqueous NH4Cl and extracted with ether. The combined organic layers were washed with H2O and brine, then dried over Na2SO4 and concentrated under vacuum. Purification by MPLC (80 g column, 0 to 40% ethyl acetate in hexane as eluant) afforded the title compound. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.65 (s, 6 H), 7.27 (dd, J=5.57 Hz, 1 H), 8.36-8.39 (m, 2 H).

後処理

  1. customthe resulting reaction mixture
  2. customThe reaction was then quenched with aqueous NH4Cl
  3. extractionextracted with ether
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customPurification by MPLC (80 g column, 0 to 40% ethyl acetate in hexane as eluant)

出典と根拠

ORDレコード
ord-0b1a3deffe2544b0bbea81136c189aaa
出典データセット
uspto-grants-2014_04
特許番号
US08703797B2

反応ノート

読み込み中…