Homoallyl bromide → HCID 58868532, compound

HRID 400336Notes

Reaction equation

HRID 400336 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C=O)C.C(OCC)(=O)C>[O:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:19][CH2:18][CH:17]=[CH2:16])[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:12]

Participants

6

Reactant 3

HCID 21241Homoallyl bromideHCID 24758Sodium hydrideHCID 5281426Umbelliferone

Product 1

HCID 58868532HCID 58868532, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-hydroxycoumarin (3 g, 19.6 mmol) in DMF (20 ml) is treated with NaH (60% suspension in oil, 1.03 g, 25.9 mmol), then with 4-bromo-1-butene (2.65 g, 19.6 mmol). It is heated to 60° C. for 24 hours, then it is diluted with ethyl acetate (400 ml), and it is washed with water (3×300 mL) then with 1 M NaOH (3×200 ml). The residue is chromatographed with the mixture (ethyl acetate-hexane) to obtain 4-(7-coumarinyloxy)-1-butene (2.7 g, 67%).

Workup

  1. washis washed with water (3×300 mL)
  2. customThe residue is chromatographed with the mixture (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c181300b85774c64a75f7795a498911c
Source dataset
uspto-grants-2014_06
Patent number
US08741593B2

Reaction notes

Loading…