3-Nitrobenzaldehyde → HCID 54394823, compound

HRID 1905373Notes

Reaction equation

HRID 1905373 reaction equation
[CH2:1]([P:5]1(=[O:13])[O:10][C@H:9]([CH3:11])[CH2:8][C@@H:7]([CH3:12])[O:6]1)[C:2]([CH3:4])=[O:3].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].N1CCCCC1.C(OCC)(=O)C.CO>C1C=CC=CC=1>[C:2]([C:1]([P:5]1(=[O:13])[O:6][C@H:7]([CH3:12])[CH2:8][C@@H:9]([CH3:11])[O:10]1)=[CH:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1)(=[O:3])[CH3:4]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 10465562HCID 10465562, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 54394823HCID 54394823, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.38 g of 2-acetonyl-(4R,6R)-4,6-dimethyl-1,3,2-dioxaphosphorinane-2-oxide and 2.4 g of m-nitrobenzaldehyde were dissolved in 15 ml of benzene, and 0.5 ml of piperidine was added thereto. The mixture was refluxed for 5 hours. The reaction solution was subjected to silica gel chromatography (developer solution: ethyl acetate/methanol=9/1 (v/v), Rf value: 0.4) to obtain 1.78 g of desired 2-(1-acetyl-2-(3-nitrophenyl)ethenyl)-(4R,6R)-4,6-dimethyl-1,3,2-dioxaphosphorinane-2-oxide as a yellow viscous liquid.

Workup

  1. temperatureThe mixture was refluxed for 5 hours

Sources & evidence

ORD record
ord-395d981f5143444dab7e83c045f3953e
Source dataset
uspto-grants-1989_06
Patent number
US04843076

Reaction notes

Loading…