1,4-Dioxane → HCID 21874588, compound

HRID 750545Notes

Reaction equation

HRID 750545 reaction equation
[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

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 21874711HCID 21874711, compound

Product 1

HCID 21874588HCID 21874588, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-13bd556bad0c44f9a1d1b534bfafd783
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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