Triethyl phosphonoacetate → HCID 69159682, compound

HRID 459848Notes

Reaction equation

HRID 459848 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:37]=[CH:36][C:33]([CH:34]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate

Product 1

HCID 69159682HCID 69159682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 60% sodium hydride and THF were added dropwise ethyl diethylphosphonoacetate and further 4-[4-(t-butoxycarbonyl)piperazin-1-yl]benzaldehyde under cooling to 0° C., followed by stirring. Then, post-treatment and purification were carried out in a usual way to obtain ethyl 3-{4-[4-(t-butoxycarbonyl)piperazin-1-yl]phenyl}acrylate. Further, catalytic reduction was carried out using palladium/carbon to obtain an objective compound.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-51128d431a774e828a5c7c31af85aa11
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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