Water → HCID 21034016, compound

HRID 734343Notes

Reaction equation

HRID 734343 reaction equation
[Li]CCCC.[CH3:6][C:7](=[N:9][OH:10])[CH3:8].[Br:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=O)=[CH:14][CH:13]=1.O>C1COCC1>[Br:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]2[O:10][N:9]=[C:7]([CH3:8])[CH:6]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12081Methyl 4-bromobenzoateHCID 67180Acetone, oximeHCID 178418339Butyllithium

Product 1

HCID 21034016HCID 21034016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-BuLi (81 ml of a 1.6M solution in hexanes) was added to a solution of acetone oxime (4.85 g) in THF (100 ml) at 0° C. The reaction mixture was allowed to warm to rt over 1 h. A solution of methyl 4-bromobenzoate (9.4 g) in THF (30 ml) was then added to the reaction mixture and allowed to stir for 24 h. Water (50 ml) was added to the reaction, the organics were extracted and evaporated to give a brown oil, which was further evaporated from toluene (2×25 ml). The crude product was purified by column chromatography (silica gel, 10-25% gradient of EtOAc in hexane) to give the title compound (D39) as a pale yellow solid (5.4 g). LCMS electrospray (+ve) 239 (MH+).

Workup

  1. extractionthe organics were extracted
  2. customevaporated
  3. customto give a brown oil, which
  4. customwas further evaporated from toluene (2×25 ml)
  5. customThe crude product was purified by column chromatography (silica gel, 10-25% gradient of EtOAc in hexane)

Sources & evidence

ORD record
ord-2f715a1e22844a7b8933dd6e8f9f1274
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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