1-(2-pyridyl)-1-[2,6-di(tetrahydro-2H-2-pyranyloxymethyl)phenyl]-methanol → 1-(2-Pyridyl)-1-[2,6-di(hydroxymethyl)-phenyl]methanol

HRID 742498Notes

Reaction equation

HRID 742498 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[C:14]([CH2:15][O:16]C2CCCCO2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:23][O:24]C1CCCCO1)[OH:8]>C(O)(=O)C.C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[C:10]([CH2:23][OH:24])=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:15][OH:16])[OH:8]

Participants

3

Reactant 1

HCID 100703421-(2-pyridyl)-1-[2,6-di(tetrahydro-2H-2-pyranyloxymethyl)phenyl]-methanol

Product 1

HCID 117766291-(2-Pyridyl)-1-[2,6-di(hydroxymethyl)-phenyl]methanolYield 43.8%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 1 g (2.42 mmol) of 1-(2-pyridyl)-1-[2,6-di(tetrahydro-2H-2-pyranyloxymethyl)phenyl]-methanol in 14 ml of acetic acid/THF/water (4:2:1) was heated at 100° C. under nitrogen for 6 hours. The mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate and concentrated in vacuo. The residual solid was triturated with ether to afford 0.26 g of 1-(2-pyridyl)-1-[2,6-di(hydroxymethyl)-phenyl]methanol (Formula X: R1 =R2 =H; R7 =6-hydroxymethyl) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe residual solid was triturated with ether

Sources & evidence

ORD record
ord-ee1632ef1b4d4dc2a4af196f6c1f1d27
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

Loading…