Sodium borohydride → HCID 15522057, compound

HRID 1859028Notes

Reaction equation

HRID 1859028 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][CH2:11][CH2:10][C:9]2=O)([O-:3])=[O:2].[BH4-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][CH2:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 186797008-Nitro-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 15522057HCID 15522057, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 g of 8-nitro-4-chromanone and 3.9 g of sodium borohydride in 200 ml of ethanol is heated at reflux for 45 minutes and then evaporated to dryness. The residue is taken up in 200 ml of water and extracted three times with 250 ml of dichloromethane each time. The combined organic phases are dried over magnesium sulphate, filtered and then concentrated under reduced pressure. The liquid residue is taken up in 300 ml of toluene; 0.5 g of para-toluenesulphonic acid is then added and heating at reflux is carried out until the full amount of water expected has been recovered. After cooling, washing with a 5% sodium carbonate solution and then with water, and concentrating under reduced pressure, a liquid residue corresponding to the expected product is isolated.

Workup

  1. temperatureat reflux for 45 minutes
  2. customevaporated to dryness
  3. extractionextracted three times with 250 ml of dichloromethane each time
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. addition0.5 g of para-toluenesulphonic acid is then added
  8. temperatureheating
  9. temperatureat reflux
  10. customexpected has been recovered
  11. temperatureAfter cooling
  12. washwashing with a 5% sodium carbonate solution
  13. concentrationwith water, and concentrating under reduced pressure

Sources & evidence

ORD record
ord-a571f1ce06fd42c4979d73a586f5ec89
Source dataset
uspto-grants-2000_11
Patent number
US06153625

Reaction notes

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