7-Methoxy-5,11-dioxa-benzo[b]fluoren-10-one → 7-Hydroxy-5,11-dioxa-benzo[b]fluoren-10-one

HRID 411659Notes

Reaction equation

HRID 411659 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7](=[O:18])[C:8]3[O:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]=3[O:17][C:5]=2[CH:4]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>>[OH:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7](=[O:18])[C:8]3[O:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]=3[O:17][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 120191237-Methoxy-5,11-dioxa-benzo[b]fluoren-10-oneHCID 67725173Pyr-HCl

Product 1

HCID 120191247-Hydroxy-5,11-dioxa-benzo[b]fluoren-10-oneYield 54.8%

Procedure

The starting methyl ether 18 (0.55 g, 2.1 mmol) was heated at 200° C. with Pyr-HCl (5 g) for one hour. The reaction mixture was allowed to cool to rt and worked up by partitioning between 2N HCl and EtOAc/MeOH. The organic layer was washed with NaHCO3 aq and brine and dried over MgSO4. Concentration gave 24 (0.29 g) as a tan solid: MP>300° C.; 1H NMR (DMSO-d6) δ 11.2 (br s, 1H), 8.14-8.07 (m, 2H), 7.87 (d, 1H, J=8.5 Hz), 7.76-7.70 (m, 1H), 7.55-7.52 (m, 1H), 7.09 (d, 1H, J=1.9 Hz), 7.02 (dd, 1H, J=8.8 Hz, 1.9 Hz); MS APCI 253 (M+H)+.

Workup

  1. customby partitioning between 2N HCl and EtOAc/MeOH
  2. washThe organic layer was washed with NaHCO3 aq and brine
  3. dry with materialdried over MgSO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-6d3d7c0105584f20afc722f71d1c3822
Source dataset
uspto-grants-2003_05
Patent number
US06559177B2

Reaction notes

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