Trimethyl phosphonoacetate → Methyl(E)-3-(2-methyl-5-nitro-phenyl)prop-2-enoate

Reaction equation

[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:13][O:14][C:15]([CH2:17]P(OC)(OC)=O)=[O:16]>>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1/[CH:4]=[CH:17]/[C:15]([O:14][CH3:13])=[O:16]

Participants

Reactant 2

HCID 80029Trimethyl phosphonoacetate

HCID 126541452-Methyl-5-nitrobenzaldehyde2×

Product 1

HCID 118276893Methyl(E)-3-(2-methyl-5-nitro-phenyl)prop-2-enoate

Procedure

Methyl(E)-3-(2-methyl-5-nitro-phenyl)prop-2-enoate (15a) is prepared from commercial 2-methyl-5-nitro-benzaldehyde (5j) (for a synthesis of (5j) see also Example 5, Method B) and commercial trimethyl phosphonoacetate as described in Example 2.

Sources & evidence

ORD record: ord-e4bc85c6938d4d70842bbf91a719f581
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394236B2

Reaction notes

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