Sodium cyanoborohydride → HCID 19918528, compound

HRID 2253968Notes

Reaction equation

HRID 2253968 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=O)[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:13][CH:12]=3)=[CH:7][C:6]=2[CH:26]=1.C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:15][CH:16]=3)=[CH:7][C:6]=2[CH:26]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 19918524HCID 19918524, compound

Product 1

HCID 19918528HCID 19918528, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

5-Bromo-2-(4-benzyloxybenzoyl)benzofuran (9.0 g, 22 mmol), sodium cyanoborohydride (10.4 g, 0.17 mol), zinc iodide (10.5 g, 0.35 mol) and 1,2-dichloroethane (350 ml) were combined and heated to reflux for 6 hours. The mixture was cooled, quenched with saturated ammonium chloride (500 ml), acidified with concentrated HCl and stirred for 30 minutes. The layers were separated, the aqueous layer was extracted with dichloromethane (400 ml) and the combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated, leaving a white solid (8.5 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. customquenched with saturated ammonium chloride (500 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane (400 ml)
  7. washthe combined organic layers were washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3ab1c4c820ec4bfa8e927edc073fdb2d
Source dataset
uspto-grants-1993_08
Patent number
US05232945

Reaction notes

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