Acetic Anhydride → Acetic Acid 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-yl Ester

HRID 31259Notes

Reaction equation

HRID 31259 reaction equation
[CH3:1][C:2]([O:4][C:5]([CH3:7])=O)=[O:3].[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[O:24][CH:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)CC3O)=[N:15][CH:16]=1)([O-:10])=[O:9]>N1C=CC=CC=1>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:27]=[C:26]3[C:25](=[CH:20][CH:19]=2)[O:24][CH:23]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:7][CH:5]3[O:4][C:2](=[O:3])[CH3:1])=[N:15][CH:16]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 179785596-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-ol

Product 1

HCID 69254709Acetic Acid 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-yl Ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetanhydride (0.26 ml) was added dropwise into a solution of 100 mg of 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-ol (Example 8(b)) in dry pyridine. The reaction mixture was refluxed for 1½ hours. It was then poured in ice-water and extracted with ethyl acetate. The organic phase was washed with 1 M HCl-solution, water and saturated NaCl-solution. It was then dried with MgSO4 and evaporated to dryness. 1H NMR (400 MHz, d6-DMSO) δ: 9.05 (d, 1H, J 2.8 Hz), 8.61 (dd, 1H, J 9.1, 2.8 Hz), 7.52-7.35 (m, 5H), 7.23 (d, 1H, J 9.1 Hz), 7.14-7.10 (m, 2H), 6.98 (d, 1H, J 8.5 Hz), 6.18 (dd, 1H, J 10.1, 6.4 Hz), 5.44(dd, 1H, J 11.4, 1.4Hz), 2.51 (m, 1H), 2.15 (m, 1H), 2.05 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 1½ hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1 M HCl-solution, water and saturated NaCl-solution
  4. dry with materialIt was then dried with MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-801014953ef14d6b97f3c596335cec8b
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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