HCID 20266223, compound → HCID 13457046, compound

HRID 1719984Notes

Reaction equation

HRID 1719984 reaction equation
[C:1]([C:4]1[CH:21]=[C:20]2[C:7]([C:8](=[O:26])[C:9]3[CH:10]([OH:25])[CH:11]4[C:16](=[C:17]([OH:22])[C:18]=3[CH2:19]2)[CH2:15][CH2:14][CH2:13][CH:12]4[O:23][CH3:24])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>CN(C)C=O>[C:1]([CH:4]1[CH2:21][C:20]2[CH:19]=[C:18]3[C:9]([C:10](=[O:25])[C:11]4[C:12]([O:23][CH3:24])=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:22])=[C:8]([OH:26])[C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 20266223HCID 20266223, compound

Product 1

HCID 13457046HCID 13457046, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (7) (0.4 g, 1.1 mmol) in dimethylformamide (40 mL) was heated at 110° C. Simultaneously, oxygen was bubbled through it. After 2 hours, flow of oxygen was terminated and 2 mL of water was added. Upon cooling, the reaction mixture gave orange crystals of (8). ##STR12## These crystals were collected by filtration, washed with water and dried: yield 0.37 g (94% yield) of (8) with mp 222°-225° C. (lit. mp 223°-226° C.), 1H NMR (CDCl3) δ 13.36 (s, 1H), 8.08-7.22 (m, 4H), 4.07 (s, 3H), 3.30-2.40 (m, 4H), 2.27 (s, 3H), 2.27 (m, 1H), 2.0-1.4 (m, 2H), mass spectrum, m/z 350 (M+). Anal. Calcd. for C21H18O5 (350.35): C, 71.99; H, 5.18. Found: C, 71.70; H, 5.30.

Workup

  1. customSimultaneously, oxygen was bubbled through it
  2. customflow of oxygen was terminated
  3. addition2 mL of water was added
  4. temperatureUpon cooling

Sources & evidence

ORD record
ord-b7894cfc6b784544a1ff38544e8ac9b9
Source dataset
uspto-grants-1985_09
Patent number
US04543428

Reaction notes

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