Sodium cyanoborohydride → HCID 19918528, compound

HRID 1464818Notes

Reaction equation

HRID 1464818 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-68ecc7e4c3464d4aafa1818349bd9147
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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