Dimethylformamide → HCID 19775673, compound

HRID 1613261Notes

Reaction equation

HRID 1613261 reaction equation
[H-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].CN(C)C=[O:27]>>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][O:27][C:7]1[CH:8]=[CH:3][CH:4]=[CH:5][C:6]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 5284650trans-4-Hydroxystilbene

Product 1

HCID 19775673HCID 19775673, compoundYield 75%

Procedure

To a suspension of sodium hydride (60%, 1.5 g, 38 mmol) in 200 ml dimethylformamide was added p-hydroxystilbene (5 g, 25 mmol), portionwise. The mixture was stirred at room temperature for 2 hours and 1-bromo-4-chlorobutane (4.4 mL, 38 mmol) was added. The mixture was then stirred at room temperature overnight. The reaction was quenched with methanol (10 mL) and filtered through Celite®. The filtrate was taken up in ether (250 mL), washed thrice with water (150 mL) and dried over sodium sulfate. The solution was concentrated to give 8.2 g (75%) of (E)-4-chlorobutoxystilbene as an amber oil. 1H NMR (CDCl3): δ7.62-6.81 (m,11H), 4.02 (t,2H), 3.63 (t,2H), 1.99 (m,4H).

Workup

  1. stirringThe mixture was then stirred at room temperature overnight
  2. customThe reaction was quenched with methanol (10 mL)
  3. filtrationfiltered through Celite®
  4. washwashed thrice with water (150 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-c8e446420b324a4ebd770d80b505c401
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

Loading…