Tetrahydrofuran → 5-Ethyl-2-fluoropyridine-3-carbaldehyde

HRID 1866120ノート

反応式

HRID 1866120 の反応式
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([F:9])=[N:7][CH:8]=1)[CH3:2].[O:10]1CCC[CH2:11]1>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:11]=[O:10])[C:6]([F:9])=[N:7][CH:8]=1)[CH3:2]

参加物

3

反応物 2

HCID 8028TetrahydrofuranHCID 210304025-Ethyl-2-fluoropyridine

生成物 1

HCID 860856655-Ethyl-2-fluoropyridine-3-carbaldehyde

実験手順

A solution of diisopropylainine (1.01 mL, 7.19 mmol) in tetrahydrofuran (20 mL) was treated in ice-bath with n-butyllithiuin (2.5M, 2.9 mL, 7.19 mmol) and stirred for 30 min. The resulting solution was reacted at −78° C. with 5-ethyl-2-fluoropyridine (2-b, 0.75 g, 5.99 mmol), stirred for 4 h, and treated with N,N-dimethylforninamide (482 mg, 6.59 mmol). The reaction mixture was quenched with acetic acid (1 mL), partitioned between ethyl acetate and water. The organic layer was washed with 0.5N—HCl and then with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (30% ethyl acetate in hexanes) afforded the desired compound (2-f); 1H NMR (500 MHz, CDCl3) δ10.3 (s, 1H), 8.29 (d, 1H, J=2.0 Hz), 8.12 (dd, 1H, J=9.0, 2.5 Hz), 2.73 (q, 2H, J =7.8 Hz), 1.29 (t, 3H, J=7.5 Hz).

後処理

  1. stirringstirred for 4 h
  2. additiontreated with N,N-dimethylforninamide (482 mg, 6.59 mmol)
  3. customThe reaction mixture was quenched with acetic acid (1 mL)
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with 0.5N—HCl
  6. customwith brine, separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d20b439877d34707b5636982f854b301
出典データセット
uspto-grants-2009_12
特許番号
US07629367B2

反応ノート

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