Butyl bromide → HCID 17993053, compound

HRID 2238691Notes

Reaction equation

HRID 2238691 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4]1.[H][H].Br[CH2:13][CH2:14][CH2:15][CH3:16]>CN(C)C=O.O>[CH2:13]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][S:3][CH:4]=1)[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 123570Thiophene-3-methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 17993053HCID 17993053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (NaH) (2.63 grams, 66 mmol, 60 percent dispersion in oil) in anhydrous N,N-dimethylformamide (DMF) (15 milliliters) was added dropwise a solution of 3-thiophenemethanol (5.105 grams, 43.8 mmol) in DMF (15 milliliters). The reaction mixture was stirred until the evolution of hydrogen ceased (about 0.5 hour). To the resulting suspension, 1-bromobutane (10.3 grams, 75 mmol) in DMF (15 milliliters) was added dropwise and then stirred at room temperature for 4 hours. The reaction mixture was poured into water (200 milliliters) and extracted with ether/hexane (v/v, 100 milliliters/100 milliliters), and washed with brine. The resulting organic layer was dried over magnesium sulfate (MgSO4) and filtered. After removing the DMF solvent, a light yellow liquid was obtained, which was subjected to column chromatography on a silica gel using first hexane (about 400 milliliters to remove mineral oil), and then hexane/CH2Cl2(dichloromethane) (v/v=1/1; 1,200 milliliters). After evaporating the solvents, a colorless liquid was obtained.

Workup

  1. custom(about 0.5 hour)
  2. extractionextracted with ether/hexane (v/v, 100 milliliters/100 milliliters)
  3. washwashed with brine
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customAfter removing the DMF solvent
  7. customa light yellow liquid was obtained
  8. customAfter evaporating the solvents
  9. customa colorless liquid was obtained

Sources & evidence

ORD record
ord-7a1599098bd64124856b1734b8f38dd8
Source dataset
uspto-grants-2010_05
Patent number
US07718999B2

Reaction notes

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