Water → tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

HRID 626413Notes

Reaction equation

C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].O>C1COCC1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:24]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. and with cooling, 156.32 g (620 mmol) of tert-butyl diethylphosphonoacetate were added dropwise to a suspension of 23.71 g (593 mmol) of sodium hydride (60% in mineral oil) in 1.0 liters of THF. After the addition had ended, the mixture was stirred at 0° C. for 30 min and a solution of 100.0 g (539 mmol) of 4-chloro-3-nitrobenzaldehyde in 200 ml of THF was then added. The reaction mixture was heated at RT overnight, and water and ethyl acetate were then added. The organic phase was removed, dried with magnesium sulphate and concentrated under reduced pressure. The residue was recrystallized from isopropanol. Drying under high vacuum gave 144.0 g (94.2% of theory) of the target product.

Workup

additionAfter the addition
temperatureThe reaction mixture was heated at RT overnight
customThe organic phase was removed
dry with materialdried with magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from isopropanol
customDrying under high vacuum
customgave 144.0 g (94.2% of theory) of the target product

Sources & evidence

ORD record: ord-ea216490ed04416c817834769560509a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309198B2

Reaction notes

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