Sodium Iodide → HCID 13423316, compound

HRID 1284473Notes

Reaction equation

HRID 1284473 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[C:12]1(/[C:18](/[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-].[Na+].C([BH3-])#N.[Na+]>CN(C)P(N(C)C)(N(C)C)=O.O>[C:12]1(/[C:18](/[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 5003444Sodium cyanoborohydrideHCID 13417327HCID 13417327, compound

Product 1

HCID 13423316HCID 13423316, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

p-Toluenesulfonate of (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol (0.45 g, 1.07 mmoles) was dissolved in hexamethylphosphoramide (2 ml), and sodium iodide (0.2 g, 1.3 mmoles) was added to the solution. The mixture was stirred for 10 minutes. To the mixture was added sodium cyanoborohydride (0.1 g, 16 mmoles) and the resulting mixture was stirred at 100° C. for an hour. The reaction mixture was then cooled and water (10 ml) was added followed by extraction of the product with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using isopropyl ether-ethyl acetate (4:1) as the eluent to give (E)-1-phenyl-1-(3-pyridyl)-1-heptene (0.2 g, 75%) as an oil.

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for an hour
  2. temperatureThe reaction mixture was then cooled
  3. extractionfollowed by extraction of the product with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3201fb97c8b2410da3075aa609539a90
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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