HCID 1622515, compound → 9-Methoxy-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 1976116Notes

Reaction equation

HRID 1976116 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:5][CH2:6][CH2:7][CH2:8][C:9](=[O:11])[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 1622515HCID 1622515, compound

Product 1

HCID 146616269-Methoxy-3,4-dihydro-1-benzoxepin-5(2H)-oneYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To PPA in toluene at 100° C., was added 4-(2-methoxyphenoxy)butanoic acid and the mixture stirred overnight. The mixture was poured onto ice-water, and extracted with ether (3 times). The combined organic phase was washed with water and dried over anhydrous sodium sulfate. Evaporation of the organic phase afforded a light yellow oil in 10% yield: 1H NMR δ 7.33 (dd, 1H, J=4.4, 5.1 Hz), 7.03 (d, 2H, J=4.3 Hz), 4.31 (t, 2H, J=6.6 Hz), 3.90 (s, 3H), 2.90 (t, 2H, J=6.9 Hz), 2.22 (p, 2H, J=6.8 Hz).

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with ether (3 times)
  3. washThe combined organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the organic phase
  6. customafforded a light yellow oil in 10% yield

Sources & evidence

ORD record
ord-99d5ce946f19492b98e37e75f066396e
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

Loading…