Acetic Anhydride → (7-Acetoxy-2-oxo-2H-chromen-4-yl)-acetic acid

HRID 270532Notes

Reaction equation

HRID 270532 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][C:14]([OH:16])=[O:15])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][C:14]([OH:16])=[O:15])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53384907-Hydroxycoumarin-4-acetic acid

Product 1

HCID 12514017(7-Acetoxy-2-oxo-2H-chromen-4-yl)-acetic acidYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 9 (1 g, 4.53 mmol) was added 25 ml of acetic anhydride and 5 ml of pyridine, and the reaction was allowed to stir at RT for 30 minutes. Upon removal of solvent in vacuo, the residue was taken into ethyl acetate and washed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to afford 10 (30% yield). 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=8.9 Hz, 1H), 7.23 (d, J=5.6 Hz, 1H), 7.24 (s, 1H), 6.47 (s, 1H), 2.94 (s, 2H), 2.33 (s, 3H). MS (ESI): m/z 263.0 [(M+H)]+.

Workup

  1. customUpon removal of solvent in vacuo
  2. washwashed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-218ce70186b0469dba86d78134e3ec95
Source dataset
uspto-grants-2008_11
Patent number
US07449558B2

Reaction notes

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