N-(3-formyl-4-methoxybenzyl)phthalimide → N-(4-methoxy-3-vinylbenzyl)phthalimide

HRID 47301Notes

Reaction equation

HRID 47301 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH:7]([C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:28][O:27][C:26]1[CH:25]=[CH:24][C:11]([CH2:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])=[CH:10][C:9]=1[CH:7]=[CH2:1]

Participants

5

Reactant 2

HCID 22744477N-(3-formyl-4-methoxybenzyl)phthalimideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22744604N-(4-methoxy-3-vinylbenzyl)phthalimideYield 39.5%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.99 g of potassium-t-butoxide was added to 80 ml solution of 12.7 g methyltriphenyl phosphonium bromide in tetrahydrofuran at 0° C., 7 g of N-(3-formyl-4-methoxybenzyl)phthalimide was added thereto, and the mixture was stirred at room temperature for 1 hr. The reaction solution was filtered through Celite, and then evaporated. The resulting residue was purified by silica gel column chromatography to give 2.75 g of N-(4-methoxy-3-vinylbenzyl)phthalimide.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customevaporated
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-be69cbf77dbd4f91ae65c0e1692f8245
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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