1,4-Dioxane → HCID 21874588, compound

HRID 733019Notes

Reaction equation

HRID 733019 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-456c21773c594ffa8fda3cbf4721071e
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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