2′-Hydroxychalcone → HCID 11805918, compound

HRID 1462954Notes

Reaction equation

HRID 1462954 reaction equation
O[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4](=[O:13])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)C>[O:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]1[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:2]=1

Participants

4

Reactant 2

HCID 146112′-HydroxychalconeHCID 4311764Sodium borohydride

Product 1

HCID 11805918HCID 11805918, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2'-Hydroxychalcone (9.0 g) was stirred with ethanol (100 ml) at room temperature whilst sodium borohydride (3.05 g) was added in small portions. After 2 hr. stirring the colourless solution was evaporated to dryness and acetic acid (100 ml) added. Toluene sulphonic acid (1.0 g) was added and the solution was heated on the steam bath for 30 min. The solution was diluted with water and extracted with toluene. The extract was washed with saturated sodium bicarbonate solution, dried over magnesium sulphate, and evaporated. The residue was chromatographed on neutral alumina to yield flav-3-ene (6.3 g) as an oil, identified by its n.m.r. spectrum. The multiplet at 5.8 p.p.m. is characteristic of flav-3-enes.

Workup

  1. additionwas added in small portions
  2. customwas evaporated to dryness and acetic acid (100 ml)
  3. additionadded
  4. additionToluene sulphonic acid (1.0 g) was added
  5. temperaturethe solution was heated on the steam bath for 30 min
  6. additionThe solution was diluted with water
  7. extractionextracted with toluene
  8. washThe extract was washed with saturated sodium bicarbonate solution
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe residue was chromatographed on neutral alumina

Sources & evidence

ORD record
ord-fa1ffa66b37f42fea7f801760edf3c61
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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