2-Methylenehexanal → HCID 54016913, compound

HRID 1682298Notes

Reaction equation

[CH2:1]=[C:2]([CH2:5][CH2:6][CH2:7][CH3:8])[CH:3]=[O:4].[CH2:9]([O:11][C:12](=[O:16])[CH2:13][N+:14]#[C-:15])[CH3:10]>>[CH2:9]([O:11][C:12]([CH:13]1[CH:3]([C:2]([CH2:5][CH2:6][CH2:7][CH3:8])=[CH2:1])[O:4][CH:15]=[N:14]1)=[O:16])[CH3:10]

Participants

Reactant 2

HCID 706122-Methylenehexanal

HCID 533707Ethyl isocyanoacetate

Product 1

HCID 54016913HCID 54016913, compound

Procedure

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

Sources & evidence

ORD record: ord-d3a3f2f2bf1f4a60bb89920abb6f6d87
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175344

Reaction notes

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