Dimethylformamide → HCID 58452906, compound

HRID 2041846Notes

Reaction equation

HRID 2041846 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].CN(C)C=O>O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 187610183-(4-Bromophenoxy)propan-1-ol

Product 1

HCID 58452906HCID 58452906, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry 100 mL round bottom flask under nitrogen was added 3-(4-bromophenoxy)propan-1-ol (9.0 g, 39.0 mmol), tert-butyldimethylsilyl chloride (7.0 g, 47.0 mmol), imidizole (3.2 g, 47.0 mmol), and 20 mL of N,N-dimethylformamide. The reaction was allowed to stir at room temperature while being monitored by thin layer chromatography. Upon disappearance of the starting material the reaction mixture was poured into a separatory funnel containing 50 mL of cold water. The product was extracted using 3×25 mL ether. The organic layers were combined and washed with 3×25 mL cold water and 3×25 mL saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate, filtered from drying agent, and the solvent was removed under reduced pressure. The material was purified by filtering through a plug of silica gel eluting with 4:6 dichloromethane:hexane. The solvent was removed under reduced pressure (12.1 g, 89.4%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=9.0 Hz, 2H), 6.76 (d, J=9.0 Hz, 2H), 4.00 (t, J=6.0 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H), 1.95 (q, J=6.0 Hz, 2H), 0.87 (s, 9H), 0.03 (s, 6H).

Workup

  1. additionUpon disappearance of the starting material the reaction mixture was poured into a separatory funnel
  2. extractionThe product was extracted
  3. washwashed with 3×25 mL cold water and 3×25 mL saturated sodium chloride solution
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customfrom drying agent
  7. customthe solvent was removed under reduced pressure
  8. customThe material was purified
  9. filtrationby filtering through a plug of silica gel eluting with 4:6 dichloromethane
  10. customThe solvent was removed under reduced pressure (12.1 g, 89.4%)

Sources & evidence

ORD record
ord-5d8db2b35d224ef6be76fa7810386f59
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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