Sodium hydride → 2',3'-Dinitro-3,4,4',5-tetramethoxy-(Z)-stilbene

HRID 896394Notes

Reaction equation

HRID 896394 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[C:4]=1[N+:14]([O-:16])=[O:15].[Br-].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+]>ClCCl>[N+:11]([C:5]1[C:4]([N+:14]([O-:16])=[O:15])=[C:3]([O:2][CH3:1])[CH:10]=[CH:9][C:6]=1/[CH:7]=[CH:23]\[C:22]1[CH:43]=[C:44]([O:48][CH3:49])[C:45]([O:46][CH3:47])=[C:20]([O:19][CH3:18])[CH:21]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 370917Triphenyl(3,4,5-trimethoxybenzyl)phosphonium bromideHCID 223492434-Methoxy-2,3-dinitrobenzaldehyde

Product 1

HCID 248541902',3'-Dinitro-3,4,4',5-tetramethoxy-(Z)-stilbeneYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methoxy-2,3-dinitrobenzaldehyde (2.94 mmol) and 3,4,5-trimethoxybenzyltriphenyl phosphonium bromide (1.54 g, 2.94 mmol, 1.0 equiv) in anhydrous dichloromethane (25 mL) was added NaH (0.424 g, 17.67 mmol, 6.0 equiv). The reaction mixture was stirred at room temperature for about 7 hours and monitored by TLC. The reaction was quenched by adding water, the organic layer was separated and the aqueous layer was extracted with dichloromethane (3×25 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to orange colored slush. To this was added about 15 mL of dichloromethane and refrigerated overnight. The crude mixture was subjected to flash chromatography to isolate 2′,3′-Dinitro-3,4,4′,5-tetramethoxy-(Z)-stilbene (0.581 g, 1.48 mmol, 51%, solid)

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×25 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to orange colored slush
  8. additionTo this was added about 15 mL of dichloromethane and refrigerated overnight

Sources & evidence

ORD record
ord-dd0d66c487704108b1553b58e1940476
Source dataset
uspto-grants-2005_07
Patent number
US06919324B2

Reaction notes

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