7,9-Dimethoxy-5-oxa-11-thia-benzo[b]fluoren-10-one → 7,9-Dihydroxy-5-oxa-11-thia-benzo[b]fluoren-10-one

HRID 411662Notes

Reaction equation

HRID 411662 reaction equation
C[O:2][C:3]1[CH:20]=[C:19]([O:21]C)[C:6]2[C:7](=[O:18])[C:8]3[S: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]=[C:19]([OH:21])[C:6]2[C:7](=[O:18])[C:8]3[S: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 101932297,9-Dimethoxy-5-oxa-11-thia-benzo[b]fluoren-10-oneHCID 67725173Pyr-HCl

Product 1

HCID 122582747,9-Dihydroxy-5-oxa-11-thia-benzo[b]fluoren-10-oneYield 72%

Procedure

Example 29 (0.26 g, 0.83 mmol) and Pyr-HCl (5 g) were heated together at 210° C. for 30 minutes. The reaction was worked up by partitioning between EtOAc/MeOH and 2N HCl aq. The organic layer was washed with brine and dried over MgSO4. The organic layer was concentrated and the product triturated with MeOH to yield the desired pdt 31 as a tan solid (0.17 g): Mp>300° C.; 1H NMR (DMSO-d6) δ 12.49 (s, 1H), 11.09 (s, 1H), 8.22 (d, 1H, J=3.4 Hz), 8.20 (d, 1H, J=4.0 Hz), 7.76-7.61 (m, 2H), 6.61 (d, 1H, J=2.1 Hz), 6.31 (d, 1H, J=2.1 Hz); MS 283 (M−H)−.

Workup

  1. customwere heated together at 210° C. for 30 minutes
  2. customby partitioning between EtOAc/MeOH and 2N HCl aq. The organic layer
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationThe organic layer was concentrated
  6. customthe product triturated with MeOH

Sources & evidence

ORD record
ord-cd3ef196673847449da4e7580c988f46
Source dataset
uspto-grants-2003_05
Patent number
US06559177B2

Reaction notes

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