Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-methyl 4-(2-nitrophenyl)but-2-enoate

HRID 716008

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]=O)([O-:3])=[O:2].[O:13]([C:15]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16])[CH3:14]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:10]=[CH:11]/[CH2:17][C:15]([O:13][CH3:14])=[O:16])([O-:3])=[O:2].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]/[CH:11]=[CH:17]/[C:15]([O:13][CH3:14])=[O:16])([O-:3])=[O:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(2-nitrophenyl)acetaldehyde (760 mg, 4.6 mmol) and methoxylcarbonylmethylenetriphenylphosphorane (1.5 g, 4.6 mmol) in toluene (10 mL) was heated at 110° C. for 3 hours. The crude material was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (2:1) to afford the title compound along with (E)-methyl 4-(2-nitrophenyl)but-2-enoate.

Workup

customThe crude material was purified by silica gel column chromatography
washeluting with hexanes and ethyl acetate (2:1)

Sources & evidence

ORD record: ord-bde7d12ffb644ed1aa14dc738b1a44a5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187483B2

Linked notes

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