Tetrahydrofuran → HCID 54192599, compound

HRID 861272Notes

Reaction equation

HRID 861272 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N:12]([CH2:14][CH:15]=[CH2:16])[CH3:13])[CH:7]=O)[CH:2]=[CH2:3].C1COCC1.[Br-].[N+:23]([C:26]1[CH:51]=[CH:50][C:29]([CH2:30][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:14]([N:12]([CH3:13])[C:11]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:30][C:29]2[CH:50]=[CH:51][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[CH:5][C:4]=1[CH2:1][CH:2]=[CH2:3])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 197008[(4-Nitrophenyl)methyl](triphenyl)phosphanium bromideHCID 19702707HCID 19702707, compound

Product 1

HCID 54192599HCID 54192599, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-allyl-4-(N-allyl-N-methylamino)benzaldehyde (10.25 g, 0.05 mol), THF (100 ml), p-nitrobenzyl triphenylphosphonium bromide (27.4 g, 0.55 mol) and water (50 ml) is mixed at room temperature while 2M sodium carbonate solution (50 ml) is added over 5 minutes. The mixture is stirred mechanically for 2 hours. The mixture is diluted with water (300 ml) and extracted two times with ether (50 ml portions). The extracts are washed with water and brine, dried over magnesium sulfate and concentrated. The mixture is diluted with toluene (100 ml) and hexane (200 ml) and the triphenyl phosphine oxide filtered off. The filtrate is concentrated and chromatographed on silica with hexane-ethyl acetate to give pure N,2-diallyl-N-methyl-4-[2-(4-nitrophenyl)ethenyl]aniline.

Workup

  1. additionis added over 5 minutes
  2. extractionextracted two times with ether (50 ml portions)
  3. washThe extracts are washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. additionThe mixture is diluted with toluene (100 ml) and hexane (200 ml)
  7. filtrationthe triphenyl phosphine oxide filtered off
  8. concentrationThe filtrate is concentrated
  9. customchromatographed on silica with hexane-ethyl acetate

Sources & evidence

ORD record
ord-695758386f9946d486a5f544a3202460
Source dataset
uspto-grants-1998_02
Patent number
US05714304

Reaction notes

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