Oxygen → HCID 59676127, compound

HRID 1880478Notes

Reaction equation

HRID 1880478 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-5a123e6e12414f9e9572564f0208c408
Source dataset
uspto-grants-2012_11
Patent number
US08318766B2

Reaction notes

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