2-Methylenepentanal → HCID 53930741, compound

HRID 1682296Notes

Reaction equation

[CH2:1]=[C:2]([CH2:5][CH2:6][CH3:7])[CH:3]=[O:4].[CH2:8]([O:10][C:11](=[O:15])[CH2:12][N+:13]#[C-:14])[CH3:9]>>[CH2:8]([O:10][C:11]([CH:12]1[CH:3]([C:2]([CH2:5][CH2:6][CH3:7])=[CH2:1])[O:4][CH:14]=[N:13]1)=[O:15])[CH3:9]

Participants

Reactant 2

HCID 706092-Methylenepentanal

HCID 533707Ethyl isocyanoacetate

Product 1

HCID 53930741HCID 53930741, compound

Procedure

The starting material is manufactured as follows: Reaction of 2-methylene-pentanal with isocyanoacetic acid ethyl ester analogously to Example 1 yields 5-(penten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester. By hydrolysis of the 5-(penten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester in a manner analogous to that described in Example 15, 2-formylamino- 3-hydroxy-4-propyl-4-pentenoic acid ethyl ester is obtained. Reaction of the 2-formylamino-3-hydroxy-4-propyl-4-pentenoic acid ethyl ester with thionyl bromide and subsequent treatment with trimethyl phosphite in a manner analogous to that described in Example 1 yields E-2-formylamino-4-propyl-5-dimethylphosphono-3-pentenoic acid ethyl ester.

Sources & evidence

ORD record: ord-83201004b58f4b14a43b6e4e20f7f837
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175344

Reaction notes

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