Tetrahydrofuran → HCID 54192599, compound

HRID 1451680Notes

Reaction equation

HRID 1451680 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 triphenyiphosphonium bromide (27.4 g, 0.55 mol) and water (50 ml) is mixed at room temperature while 2 M 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 (250 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 hexaneethyl 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 (250 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 hexaneethyl acetate

Sources & evidence

ORD record
ord-ced0a5ddb9884afaab7acc8a60189c70
Source dataset
uspto-grants-1997_02
Patent number
US05605726

Reaction notes

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