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

HRID 131093Notes

Reaction equation

HRID 131093 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-450daebe13584f93b88af5344be92bb9
Source dataset
uspto-grants-2008_06
Patent number
US07384925B2

Reaction notes

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