1,4-Dioxane → HCID 21874588, 화합물

HRID 750545노트

반응식

HRID 750545 반응식
[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

참가 물질

4

반응물 2

HCID 312751,4-DioxaneHCID 21874711HCID 21874711, 화합물

생성물 1

HCID 21874588HCID 21874588, 화합물

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-13bd556bad0c44f9a1d1b534bfafd783
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405219B2

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