Acetic Anhydride → HCID 22047292, compound

HRID 1073003Notes

Reaction equation

HRID 1073003 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:11][CH2:10][C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][O:1][C:5]2=[CH:6][N:7]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22047174Furo[2,3-c]pyridin-5-ylmethanol

Product 1

HCID 22047292HCID 22047292, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Furo[2,3-c]pyridin-5-ylmethanol (7.70 g, 51.63 mmol) is dissolved in pyridine (45 mL), treated with acetic anhydride (14.36 mL, 154.9 mmol) and stirred for 18 h at rt. The pyridine is removed in vaeuo and the resulting residue dissolved in EtOAc (200 mL), washed with 50% saturated sodium bicarbonate (4×90 mL), dried over MgSO4 and concentrated in vacuo to afford 9.32 g (94%) of furo[2,3-c]pyridin-5-ylmethyl acetate as a yellow oil. MS (EI) m/z: 191 (M+), 277, 148, 119, 118, 86, 84, 77, 63, 51, 50.

Workup

  1. customThe pyridine is removed in vaeuo
  2. dissolutionthe resulting residue dissolved in EtOAc (200 mL)
  3. washwashed with 50% saturated sodium bicarbonate (4×90 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad0ab55c429e4080b8fe76c6ee70cdbe
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

Loading…