Propargyl alcohol → 1-(3-Bromo-1,2-oxazol-5-yl)ethan-1-ol

HRID 622841Notes

Reaction equation

HRID 622841 reaction equation
[Br:1][C:2](Br)=[N:3][OH:4].[CH2:6]([OH:9])[C:7]#[CH:8].[C:10](OCC)(=O)C#C.C1(C#C)C=CC=CC=1.C#CC(O)CC.C(O)#CCCCC.C(O)CC#C.ClC(Cl)=NO.CC(O)C#C>>[Br:1][C:2]1[CH:8]=[C:7]([CH:6]([OH:9])[CH3:10])[O:4][N:3]=1

Participants

10

Reactant 9

HCID 7859Propargyl alcohol2×HCID 10821PhenylacetyleneHCID 12182Ethyl propiolateHCID 135663-Butyn-1-OLHCID 162393-Butyn-2-olHCID 65582Carbonimidic dichloride, hydroxy-HCID 929811-Pentyn-3-olHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 15256937Hex-1-yn-1-ol

Product 1

HCID 138020861-(3-Bromo-1,2-oxazol-5-yl)ethan-1-ol

Procedure

In a similar manner dibromoformaldoxime is reacted with propargyl alcohol, ethyl propiolate, phenylacetylene, 1-pentyn-3-ol, 1-hexyn-1-ol, 3-butyn-1-ol, n-butyl 2-hydroxy-3-butanoate, and dichloroformaldoxime is reacted with 3-butyn-2-ol and propargyl alcohol, to afford the following compounds respectively:

Workup

  1. customto afford the following compounds respectively

Sources & evidence

ORD record
ord-e2790176ba284dc9af7192c6e5b3f99c
Source dataset
uspto-grants-1988_09
Patent number
US04772719

Reaction notes

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