HCID 59272356, compound → HCID 59272342, compound

HRID 1970234Notes

Reaction equation

HRID 1970234 reaction equation
[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:21])[CH:15]=3)[C:10](=O)[C:9]=2[CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:21])[CH:15]=3)[C:10](=[CH2:1])[C:9]=2[CH:8]=1

Participants

5

Reactant 2

HCID 59272356HCID 59272356, compoundHCID 178418339Butyllithium

Product 1

HCID 59272342HCID 59272342, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (2664 mg, 7457 μmol) in THF (19 ml) at 0° C. was added butyllithium (1.6 M in Hexanes, 3995 μl, 6392 μmol) dropwise. After stirring at 0° C. for 30 minutes, a solution of 2-bromo-6-methyl-9H-xanthen-9-one (1540 mg, 5326 μmol) in THF (5 ml) was added dropwise. The solution was allowed to warm to RT and stirred for 1 hour. The reaction mixture was quenched with water and the aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The crude product was flashed with the MPLC (100% hexanes to 10% EtOAc in hexanes to 30% EtOAc in hexanes) MS m/z=289.1 [M+H]+. Calc'd for C15H11BrO2: 287.1.

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 1 hour
  3. customThe reaction mixture was quenched with water
  4. washthe aqueous layer was washed 3× with EtOAc
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-14018e4e914649e8b3b20cb6389c08cd
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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