Sodium hydride → HCID 70029796, compound

HRID 413425

Reaction equation

HRID 413425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25]CBr)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 858682-(3-Methoxyphenyl)cyclohexanoneHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 70029796HCID 70029796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-(3-Methoxy-phenyl)-cyclohexanone (0.80 g, 4.05 mmol) was added slowly to a suspension of NaH (60%) (0.185 g, 5.1 mmol) in anhydrous DMF (5 mL) at 0° C. under Ar over 15 min. After an additional 15 min. at 20° C. 6-bromohexanoic acid ethyl ester (1.0 g, 4.5 mmol) was added followed by stirring at 60° C. for 6 hr. The reaction mixture was cooled, quenched with saturated NH4Cl solution, partitioned between EtOAc (150 mL) and H2O (100 mL), the organic layer washed with H2O (2×100 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound after silica gel chromatography eluting with hexane:EtOAc, 50:1 to 10:1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with saturated NH4Cl solution
  3. custompartitioned between EtOAc (150 mL) and H2O (100 mL)
  4. washthe organic layer washed with H2O (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5008655f7c894778974241fa7dbec834
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Linked notes

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