Propargyl bromide → HCID 22904602, compound

HRID 2399653Notes

Reaction equation

HRID 2399653 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH2:13](Br)[C:14]#[CH:15].C1(OCC#C)C2C(=CC=CC=2)C=CC=1>[OH-].[K+].CN(C)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1[CH:13]=[CH:14][CH2:15][O:12][C:7]=1[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 271446-Bromo-2-naphthalenolHCID 29132Naphthalene, 1-(2-propynyloxy)-

Product 1

HCID 22904602HCID 22904602, compound

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 14797Potassium HydroxideSolvent

Procedure

In Reaction E, 6-bromo-2-naphthol and propargyl bromide represented by graphic formulae VIII and XVII, respectively, are refluxed together in ethanoic potassium hydroxide. The resulting propargyl naphthyl ether represented by graphic formula XVIII will, when refluxed in N,N-dimethylaniline (DMA), yield 8-bromo-3H-naphtho[2,1-b]pyran represented by graphic formula XIX. See Chromenes, Chromanones and Chromones Chapter II, E. E. Schweizer and D. Meeder-Nycz, 1977, pages 43 to 70. The conversion of 8-bromo-3H-naphtho[2,1-b]pyran to 8-hydroxy-3H-naphtho[2,1-b]pyran of graphic formula XX proceeds thru a series of steps described in Organic Synthesis Vol. 49 pages 90-93, 1972. Other substituted 8-hydroxy-3H-naphtho[2,1-b]pyrans may be synthesized by replacing propargyl bromide with another reactant such as substituted 3-bromo-1-alkynes. Coupling the resulting 8-hydroxy-3H-naphtho[2,1-b]pyran with the appropriate propargyl alcohol would result in compounds represented by graphic formula IB having formula IIC as group A. ##STR9##

Sources & evidence

ORD record
ord-4e39b34c939240f6a6b43837a1334e97
Source dataset
uspto-grants-1995_09
Patent number
US05451344

Reaction notes

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