Diboron → HCID 23468276, compound

HRID 443642Notes

Reaction equation

HRID 443642 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH:13]([CH3:28])[C:14]([NH:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)=O)=[CH:4][CH:3]=1.B#B>O1CCCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH:13]([CH3:28])[CH2:14][NH:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328200DiboronHCID 23468303HCID 23468303, compound

Product 1

HCID 23468276HCID 23468276, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold, stirred solution of ethyl p-[2-(4-chloro-1-naphthyloxy)propionamido]benzoate (9.5 g.) in 100 ml. dry tetrahydrofuran is added slowly 35 ml. of 1 M diborane in tetrahydrofuran. The reaction mixture is stirred at room temperature for 20 minutes, then refluxed for 31/2 hours. The mixture is poured onto 500 ml. of ice, giving a cloudy solution. After saturating this solution with sodium chloride, it is extracted twice with ether and twice with chloroform. The combined organic phases are dried and flash-evaporated to a yellow oil. The oil is dissolved in a small amount of ethyl acetate and hexane and purified on a column of silica gel, giving a white powder, m.p. 122° C.

Workup

  1. temperaturerefluxed for 31/2 hours
  2. additionThe mixture is poured onto 500 ml
  3. customof ice, giving a cloudy solution
  4. concentrationAfter saturating this solution with sodium chloride, it
  5. extractionis extracted twice with ether and twice with chloroform
  6. customThe combined organic phases are dried
  7. customflash-evaporated to a yellow oil
  8. dissolutionThe oil is dissolved in a small amount of ethyl acetate and hexane
  9. custompurified on a column of silica gel
  10. customgiving a white powder, m.p. 122° C.

Sources & evidence

ORD record
ord-fc4690b69c5748a1bf181b7b67780647
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

Loading…