3-Hydroxyacetophenone → HCID 22128939, compound

HRID 426396Notes

Reaction equation

HRID 426396 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18]([CH2:19][O:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)=[O:21])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22128939HCID 22128939, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 1.47 g, 36.7 mmol) in anhydrous DMF (50 mL) at 0° C. was added solid 3′-hydroxyacetophenone (5.0 g, 36.7 mmol). The mixture was stirred under N2 for 10 min and a clear yellow solution was formed. Then, tert-butylbromoacetate (6.23 mL, 38.5 mmol) was added and the mixture stirred at 0° C. for 5 min and then at room temperature for 20 min. TLC showed no starting material remaining. The mixture was partitioned between EtOAc (250 mL) and water (100 mL). The organic layer was separated, washed with saturated brine, dried (MgSO4) and concentrated in vacuo. Chromatography on silica (20% EtOAc/hexanes) gave 7.6 g (83%) of a white crystal. 1H NMR (CDCl3, 300 MHz) 7.60-7.14 (m, 4H), 4.59 (s, 2H), 2.60 (s, 3H), 1.51 (s, 9H); 13C NMR (CDCl3, 75 MHz) 198.0, 168.0, 158.6, 138.9, 130.1, 122.3, 120.6, 113.5, 83.0, 66.1, 28.4, 27.0.

Workup

  1. customa clear yellow solution was formed
  2. stirringthe mixture stirred at 0° C. for 5 min
  3. waitat room temperature for 20 min
  4. customThe mixture was partitioned between EtOAc (250 mL) and water (100 mL)
  5. customThe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2224195e7cc647acb5b0ed2793ace99d
Source dataset
uspto-grants-2012_01
Patent number
US08106191B2

Reaction notes

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