1,4-Dibromobutane → HCID 57107164, compound

HRID 481412

Reaction equation

HRID 481412 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:9]=2[CH:10]=1)[CH3:2].[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23]Br>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:5]1([C:6]2[O:7][C:8]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:9]=3[CH:10]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])[CH3:2]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 70085569(5-Methylbenzofuran-2-yl)acetic acid ethyl ester2×

Product 1

HCID 57107164HCID 57107164, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product of Step 3, above (57) (1.85 mmol), in 2 ml DMF was added 60% sodium hydride in oil (3.6 mmol) at ambient temperature. The reaction mixture was stirred for 15 minutes and then 1,4-dibromobutane (1.85 mmol) was added. The reaction mixture was heated to 80° C. for 2 hours, cooled to ambient temperature, diluted with EtOAc and washed with saturated sodium bicarbonate and brine. The combined organics were then dried over MgSO4, filtered and concentrated to dryness. The crude material was chromatographed on silica gel using 10% EtOAc in hexanes as the eluant to obtain the title compound (58).

Workup

  1. temperaturecooled to ambient temperature
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialThe combined organics were then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude material was chromatographed on silica gel using 10% EtOAc in hexanes as the eluant

Sources & evidence

ORD record
ord-2d6ceee18c7a4682a44f5c56f74fc782
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Linked notes

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