N-methyl-2-pyrrolidone → HCID 54040786, compound

HRID 485723Notes

Reaction equation

HRID 485723 reaction equation
Br[C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[C:15]([OH:16])=[CH:14][C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=1.[CH3:21][N:22]1CCCC1=O>>[C:21]([C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[C:15]([OH:16])=[CH:14][C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=1)#[N:22]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 54383517HCID 54383517, compound

Product 1

HCID 54040786HCID 54040786, compound

Procedure

6-(o-Bromocinnamyl)-2,3-dihydro-5-hydroxy-benzofuran (1.49 g; 4.5 mM) and cuprous cyanide (1.37 g; 15.3 mM) were suspended in 18 ml of anhydrous N-methyl-2-pyrollidinone. Nitrogen was bubbled through this suspension for approximately 15 minutes and the reaction mixture was then heated to 175° under nitrogen for 2 hours. After cooling to ambient temperature the reaction was poured into 60 ml of water containing 60 ml of concentrated ammonium hydroxide. This emulsion was extracted three times with ether, dried over magnesium sulfate and stripped to a brown oil. Flash chromatography of this material on a 30 mm by 51/2" column of silica gel eluted with 500 ml of 35% ethyl acetate in hexane gave a solid which was recrystallized from ethyl acetate/hexane producing 0.95 g (76%) of white crystals identified as 6-(o-cyanocinnamyl)-2,3-dihydro-5-hydroxy-benzofuran.

Workup

  1. customNitrogen was bubbled through this suspension for approximately 15 minutes
  2. temperaturethe reaction mixture was then heated to 175° under nitrogen for 2 hours
  3. additionwas poured into 60 ml of water containing 60 ml of concentrated ammonium hydroxide
  4. extractionThis emulsion was extracted three times with ether
  5. dry with materialdried over magnesium sulfate
  6. washFlash chromatography of this material on a 30 mm by 51/2" column of silica gel eluted with 500 ml of 35% ethyl acetate in hexane
  7. customgave a solid which
  8. customwas recrystallized from ethyl acetate/hexane producing 0.95 g (76%) of white crystals

Sources & evidence

ORD record
ord-26a9183666634cadbecfa1a1143f2207
Source dataset
uspto-grants-1985_08
Patent number
US04537903

Reaction notes

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