Boron trifluoride etherate → HCID 19785210, compound

HRID 256528Notes

Reaction equation

HRID 256528 reaction equation
B(F)(F)F.CCOCC.[BH4-].[Na+].[C:12]1([S:18]([N:21]2[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][N+:28]([O-])=O)=[CH:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[C:12]1([S:18]([N:21]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH2:28])=[CH:22]2)(=[O:19])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 542027321-(Benzenesulfonyl)-3-(2-nitroethenyl)-1H-pyrrole

Product 1

HCID 19785210HCID 19785210, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Boron trifluoride etherate (17.7 g) was added under nitrogen with ice-cooling to sodium borohydride (3.94 g) suspended in tetrahydrofuran (150 ml). After stirring at room temperature for fifteen minutes 2-(1-phenylsulphonyl-3-pyrrolyl)-1-nitroethylene (5.78 g) (prepared according to Synthetic Communications, 15 (1), 71-74 (1985)), dissolved in tetrahydrofuran (80 ml) was added dropwise. The mixture was refluxed overnight, quenched by the addition of ice-water, acidified with 5M hydrochloric acid and refluxed for a further two hours. The aqueous layer was washed with ether and the amine liberated by the addition of 0.880 ammonia solution which was extracted into dichloromethane. The extracts were washed with water, dried and evaporated to give pure product as an oil.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed overnight
  3. customquenched by the addition of ice-water
  4. temperaturerefluxed for a further two hours
  5. washThe aqueous layer was washed with ether
  6. additionthe amine liberated by the addition of 0.880 ammonia solution which
  7. extractionwas extracted into dichloromethane
  8. washThe extracts were washed with water
  9. customdried
  10. customevaporated
  11. customto give pure product as an oil

Sources & evidence

ORD record
ord-93a7d45912864c7d916dff9903d2e47a
Source dataset
uspto-grants-1993_11
Patent number
US05258378

Reaction notes

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