Carbon Dioxide → HCID 59676068, compound

HRID 642768Notes

Reaction equation

HRID 642768 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15]1[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[O:12][CH2:11][C:10]2=1.[C:25](=[O:27])=[O:26]>C1COCC1>[CH3:20][N:16]1[C:15]2[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[O:12][CH2:11][C:10]=2[C:9]2[C:17]1=[CH:18][CH:19]=[C:7]([C:25]([OH:27])=[O:26])[CH:8]=2

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 59676080HCID 59676080, compoundHCID 178418339Butyllithium

Product 1

HCID 59676068HCID 59676068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi was added dropwise into 8-bromo-11-methyl-6,11-dihydro-5-oxa-11-aza-benzo[a]fluorene (420 mg, 1.338 mmoL) in THF (5 mL) at −78° C. After an additional 30 minutes, the reaction mixture was transferred into dry ice (˜10 g). The reaction mixture was then slowly warmed to room temperature. The solvent was removed and the residue was partitioned between EtOAc and 1 N NaOH solution. The aqueous layer was then acidified to a pH of about 2 using 1N HCl and extracted three times with EtOAc. The organic phase of each extraction was combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a clear oil. The oil was then purified by column chromatography (silica gel, hexanes:EtOAc 1:1 as eluent) to yield the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and 1 N NaOH solution
  3. extractionextracted three times with EtOAc
  4. extractionThe organic phase of each extraction
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a clear oil
  10. customThe oil was then purified by column chromatography (silica gel, hexanes:EtOAc 1:1 as eluent)

Sources & evidence

ORD record
ord-3e391720f3b9470ab3cca7773e2d7a63
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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