Butyric Acid → Butanoic acid, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester

HRID 1589941Notes

Reaction equation

HRID 1589941 reaction equation
[C:1]([OH:6])(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=[O:18])[O:16]1.C(OCC)(=O)C>CN(C)C=O>[C:1]([O:6][CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=[O:18])[O:16]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 954693-Chlorophthalide

Product 1

HCID 10775272Butanoic acid, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of butyric acid (1.10 g., 12.5 mmol.) in dimethylformamide (13 ml.) is added triethylamine (1.78 g., 17.6 mmol.) and 3-chlorophthalide (2.10 g., 12.5 mmol.). The reaction mixture is stirred for 8 days, ethyl acetate (40 ml.) is added and the mixture is filtered. The filtrate is washed with 4×15 ml. water, dried over magnesium sulfate, filtered and concentrated in vacuo. Yield 2.28 g. (82.8%). 1H-NMR ppm (CDCl3): 7.93 (dd, J=0.7. 7.5 Hz, 1H), 7.76 (dt, J=1.1, 7.5 Hz, 1H), 7.65 (dt, J=1.0, 8.2 Hz, 1H), 7.58 (dd, J=0.7, 8.2 Hz, 1H), 7.46 (s, 1H), 2.42 (t, J=7.4 Hz, 2H), 1.72 (sextet, J=7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationthe mixture is filtered
  2. washThe filtrate is washed with 4×15 ml
  3. dry with materialwater, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fae6da05fedf4396ab89e535fbf455d1
Source dataset
uspto-grants-1993_04
Patent number
US05200553

Reaction notes

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