1,4-Dioxane → HCID 21874588、化合物

HRID 733019ノート

反応式

HRID 733019 の反応式
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:6]=1.O1CCOCC1>Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([CH2:11][OH:12])[CH:8]=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 312751,4-DioxaneHCID 21874711HCID 21874711、化合物

生成物 1

HCID 21874588HCID 21874588、化合物

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒2 回

実験手順

A solution of 2-(2-methoxyethyl)-6-(triphenylmethoxy)methylpyridine (1.08 g, 2.64 mmol) in 4-M HCl in dioxan (10 mL, 40.0 mmol) was stirred for 4 h and concentrated in vacuo. The residue was partitioned between dichloromethane (15 mL) and saturated NaHCO3 solution (15 mL), the aqueous phase was extracted with dichloromethane (10 mL) and the combined organic phase was dried (MgSO4) and concentrated in vacuo to give 6-(2-methoxyethyl)pyridine-2-methanol. A solution of this product in dichloromethane (40 mL) at 0° C. was treated with triphenylphosphine (830 mg, 3.16 mmol) followed portionwise by carbon tetrabromide (1.31 g, 3.96 mmol), stirred for 1 h, concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (4:1)] to give the title compound (303 mg, 50%) as a yellow oil; NMR δH (400 MHz, CDCl3) 7.60 (1H, t, J 7.5 Hz), 7.28 (1H, d, J 7.5 Hz), 7.13 (1H, d, J 7.5 Hz), 4.53 (2H, s), 3.76 (2H, t, J 6.5 Hz), 3.35 (3H, s) and 3.05 (2H, t, J 6.5 Hz).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between dichloromethane (15 mL) and saturated NaHCO3 solution (15 mL)
  3. extractionthe aqueous phase was extracted with dichloromethane (10 mL)
  4. dry with materialthe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-456c21773c594ffa8fda3cbf4721071e
出典データセット
uspto-grants-2009_09
特許番号
US07589097B2

反応ノート

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