Oxygen → HCID 59676127, compound

HRID 642785Notes

Reaction equation

HRID 642785 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[O:8][CH2:7][C:6]2=1.[O:20](C(C)(C)C)[K].O=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[O:8][CH:7]([OH:20])[C:6]2=1

Participants

5

Reactant 3

HCID 977OxygenHCID 619571HCID 619571, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 59676127HCID 59676127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-methoxy-6,11-dihydro-5-oxa-11-aza-benzo[a]fluorene (300 mg, 1.194 mmoL) in DMF (5 mL) was treated with KO-t-Bu (1.0 M in THF, 2.0 mL, 2.0 mmoL) under a flow of O2 for 6 hours. The reaction mixture was then partitioned between water and EtOAc. The EtOAc layer was washed with saturated NH4Cl, water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material was then purified by column chromatography (silica gel, hexanes:EtOAc 9:1 as eluent) to yield the title compound as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between water and EtOAc
  2. washThe EtOAc layer was washed with saturated NH4Cl, water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe crude material was then purified by column chromatography (silica gel, hexanes:EtOAc 9:1 as eluent)

Sources & evidence

ORD record
ord-680a88523985439b83acf779b4629514
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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